[ CAS No. 101385-93-7 ] {[proInfo.proName]}

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Quality Control of [ 101385-93-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 101385-93-7 ]

SDS Specification

Alternatived Products of [ 101385-93-7 ]

Product Details of [ 101385-93-7 ]

CAS No. :	101385-93-7	MDL No. :	MFCD01631194
Formula :	C₉H₁₅NO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JSOMVCDXPUXKIC-UHFFFAOYSA-N
M.W :	185.22	Pubchem ID :	471360
Synonyms :

Calculated chemistry of [ 101385-93-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.99
TPSA :	46.61 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.82
Log Po/w (MLOGP) :	0.45
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	0.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.21
Solubility :	11.5 mg/ml ; 0.0622 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	11.3 mg/ml ; 0.061 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.11
Solubility :	14.2 mg/ml ; 0.0767 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 101385-93-7 ]

Signal Word:	Danger	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H318-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 101385-93-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 101385-93-7 ]
Downstream synthetic route of [ 101385-93-7 ]

[ 101385-93-7 ] Synthesis Path-Upstream 1~6

1
[ 101385-93-7 ]
[ 3760-52-9 ]

Reference： [1] Patent: US2009/29963, 2009, A1, . Location in patent: Page/Page column 14
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14836 - 14843

2
[ 101385-93-7 ]
[ 365996-87-8 ]

Reference： [1] Patent: WO2006/127530, 2006, A2,

3
[ 81290-20-2 ]
[ 101385-93-7 ]
[ 644970-36-5 ]

Reference： [1] Patent: WO2004/5295, 2004, A1, . Location in patent: Page 158-159
[2] Patent: EP2540728, 2013, A1, . Location in patent: Page/Page column 76

4
[ 75-16-1 ]
[ 101385-93-7 ]
[ 412278-02-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 20℃; for 1 h; Inert atmosphere	To an ice-cold solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1.0 g, 5.40 mmol) in Et₂O (20 mL) was added methylmagnesium bromide (3.50 mL, 10.80 mmol.) drop wise under an inert atmosphere. The mixture was stirred at RT for 1 h, then quenched with NH₄Cl solution followed by extraction with EtOAc (3*100 mL). The combined organic layers were washed with brine, dried (Na₂SO₄), filtered and concentrated in vacuo. Trituration with n-pentane gave i (1.0 g, 92percent). 3-Methylpyrrolidin-3-ol hydrochloride (Precursor 52): To a solution of 4M HCl in 1,4-dioxane (10 mL) at 0° C. was added i (0.850 g, 4.22 mmol) and the mixture stirred for 2 h at RT.
83.8%	Stage #1: With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at -10℃; for 1 h; Stage #2: for 0.5 h;	(2) Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate To a 30 L reaction kettle was added 4 L dry THF at -10° C. After stirring, to the mixture were added ZnCl₂ (118 g, 0.86 mol) and LiCl (402 g, 9.5 mol). After half an hour, to the resulting mixture was slowly added a solution of MeMgBr (3 mol/L) in diethyl ether (6.4 L, 19.2 mol) dropwisely. The stirring was continued for half an hour. To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1600 g, 8.6 mol) in THF dropwisely. After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH₄Cl solution to quench off the reaction. The reaction was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale yellow solid (1450 g) in a yield of 83.8percent.
83.8%	With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether	(2) Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine -1-carboxylate To a 30 L reaction kettle was added 4 L dry THF at -10°C. After stirring, to the mixture were added ZnCl₂ (118g, 0.86mol) and LiCl (402g, 9.5mol). After half an hour, to the resulting mixture was slowly added a solution of MeMgBr (3mol/L) in diethyl ether (6.4 L, 19.2mol) dropwisely. The stirring was continued for half an hour. To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1600g, 8.6mol) in THF dropwisely. After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH₄Cl solution to quench off the reaction. The reaction was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale yellow solid (1450 g) in a yield of 83.8 percent.

83.8%	With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at -10℃; for 0.5 h;	(2) Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine -1-carboxylate To a 30 L reaction kettle was added 4 L dry THF at -10°C. After stirring, to the mixture were added ZnCl₂ (118g, 0.86mol) and LiCl (402g, 9.5mol). After half an hour, to the resulting mixture was slowly added dropwisely a solution of MeMgBr (3mol/L) in diethyl ether (6.4 L, 19.2mol). The stirring was continued for half an hour. To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine -1-carboxylate (1600g, 8.6mol) in THF dropwisely. After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH₄Cl solution to quench off the reaction. The reaction was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale-yellow solid (1450g) in a yield of 83.8 percent.
70%	at -78℃; for 4 h;	The solution of (0.070 g, 0.38 mmol) tert-butyl 3-oxopyrrolidine-l- carboxylate in anhydrous THF (2 mL) was cooled to -78°C. Then the solution of 1 M methylmagnesium bromide in butyl ether was added dropwise. The reaction was stirred at - 78°C for 4 h and quenched by water (2 mL). After concentrating the reaction in vacuo, the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted once more with ethyl acetate, and the combined organic layers were washed with brine, dried (MgSO₄) and concentrated. The residue was purified by silica flash chromatography (gradient elution, using 1 : 1 hexane-ethyl acetate and ethyl acetate) to provide the title compound (0.054 g, 70percent).
69%	at 0 - 20℃; for 1 h;	EXAMPLE 310 Synthesis of rac-4-((1-benzyl-3-methylpyrrolidin-3-yl)oxy)-5-chloro-2-fluoro-/\/-(thiazol-4-yl)benzenesulfonamide Step 1. Preparation of rac-te/f-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate To a cooled (0 °C) solution of te/f-butyl 3-oxopyrrolidine-1-carboxylate (0.975 g, 5.26 mmol) in anhydrous diethyl ether (20 mL)) was added a 3 M solution of methylmagnesium bromide in diethyl ether (3.50 mL, 10.53 mmol). The reaction was allowed to warm to ambient temperature, stirred for 1 hour, and then cooled to 0 °C and quenched by addition of saturated aqueous ammonium chloride (15 mL). The aqueous layer was separated and extracted with ethyl acetate (3 ^χ 100 mL). The combined organic phases were washed with brine (50 mL), dried with magnesium sulfate, and filtered. Concentration of the filtrate in vacuo and purification of the residue by column chromatography, eluting with a gradient of 0-40percent of ethyl acetate in hexanes, provided the title compound as a yellowish oil (0.735 g, 69percent yield) H NMR (300 MHz, CDCIs) 3.54-3.44 (m, 2H), 3.42-3.33 (m, 1 H), 3.28-3.20 (m, 1 H), 1.93-1.79 (m, 2H), 1.60-1.56 (m, 1 H), 1.46 (s, 9H), 1.42 (s, 3H); MS (ES+) m/z 202.3 (M + 1).
105 mg	at 0 - 20℃; for 1 h;	3.0 M ether solution of methylmagnesium bromide (540 .il, 1.62 mmol) wasadded to a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (100 mg, 0.540 mmol) in THF (2 ml) at 0 °C and warmed up to rt for 1 hr., quenched with saturated NH4C1 (2 ml), extracted with ethyl acetate (60 ml), washed with water, brine, dried (MgSO4) andconcentrated under reduced pressure to provide tert-butyl 3 -hydroxy-3 -methylpyrrolidine1-carboxylate (105 mg) which was used as such for the next step without purification. ‘H NMR (400MHz, CDC13) ? ppm 3.60 - 3.18 (m, 4H), 1.97 - 1.80 (m, 2H), 1.56 - 1.38 (m, 12H).

Reference： [1] Patent: US2013/252938, 2013, A1, . Location in patent: Paragraph 0514
[2] Patent: US2014/45896, 2014, A1, . Location in patent: Paragraph 0134; 0135; 0199; 0200
[3] Patent: EP2703398, 2014, A1, . Location in patent: Paragraph 0119; 0120
[4] Patent: EP2703398, 2014, A1, . Location in patent: Paragraph 0173; 0174
[5] Journal of the American Chemical Society, 2015, vol. 137, # 35, p. 11270 - 11273
[6] Patent: WO2008/24725, 2008, A1, . Location in patent: Page/Page column 123
[7] Patent: WO2017/201468, 2017, A1, . Location in patent: Page/Page column 420-421
[8] Patent: WO2015/35278, 2015, A1, . Location in patent: Page/Page column 87

5
[ 101385-93-7 ]
[ 74-88-4 ]
[ 412278-02-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With iodine; magnesium In diethyl ether at 0 - 20℃; for 1.5 h; Inert atmosphere	To a stirred suspension of magnesium (2.59 g, 106 mmol, 1.97 equiv) in 50 mL of dry ether were added iodine (catalytic) and methyl iodide (6.7 mL, 108 mmol, 2 equiv) slowly drop wise at 0°C under argon atmosphere. This was added to a solution of tert-butyl 3- oxopyrrolidine-1-carboxylate (10 g, 54 mmol, 1 equiv) in 50 mL of ether at 0°C. The reaction mixture was warmed to room temperature and stirred for 1.5 h. After completion, the reactionwas quenched with saturated ammonium chloride solution at 0 °C and extracted with EtOAc. The combined organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification using silica gel column chromatography (20percent EtOAc hexanes) afforded 7.0 g of tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate (Yield = 64percent).
48%	Stage #1: With magnesium In diethyl ether Stage #2: at 0 - 20℃; for 1.5 h; Stage #3: With water; ammonium chloride In diethyl ether at 0℃;	c) tert-Bntyl S-hydroxy-S-methylpyrrolidine-l-carboxylate; Methyl magnesium iodide [prepared from magnesium metal (1.73 g, 0.071 mol) and methyl iodide (4.7 mL, 0.074 mol) in dry ether (50 mL)] was slowly added to the solution of step b) product (6.6 g, 0.036 mol) in dry ether (150 mL) at 0 ⁰C under nitrogen atm. The reaction mixture was slowly warmed to RT and stirred for 1.5 h and after cooling to 0 ⁰C, it was quenched with saturated NH₄Cl solution. The two layers were separated and the aqueous layer was extracted with ethyl acetate (3xl00mL). The combined organic layers were washed with brine, dried over Na₂SO₄ and concentrated. The crude product was purified by column chromatography using 40 percent EtOAc in pet. ether. Yield =3.4 g (48 percent). The product was used directly in step d).

Reference： [1] Patent: WO2016/100940, 2016, A1, . Location in patent: Page/Page column 151
[2] Patent: WO2007/11284, 2007, A1, . Location in patent: Page/Page column 29

6
[ 917-64-6 ]
[ 101385-93-7 ]
[ 412278-02-5 ]

Reference： [1] Patent: US2014/45896, 2014, A1, . Location in patent: Paragraph 0081; 0082

[ 101385-93-7 ] Synthesis Path-Downstream 1~13

1
[ 146256-98-6 ]
[ 101385-93-7 ]

Yield	Reaction Conditions	Operation in experiment
10.8 g	With 2,6-di-tert-butyl-4-methyl-phenol; In water; dimethyl sulfoxide; toluene; for 6h;	Ethyl N-Boc pyrrolidonecarboxylate (20.0 g) (compound of formula (II) wherein R is Et) was dissolved in toluene (30 ml) and dimethylsulfoxide Mixture and 20 mg of 3,5-di-tert-butyl-4-hydroxytoluene (BHT) was added.The resulting mixture was heated to 115 ° C (internal temperature) and water (4.2 ml, 3.0 eq) was added dropwise over 5 h maintaining the internal temperature at 110-115 ° C.The desired conversion was achieved 1 hour after the water addition was completed.The reaction mixture was cooled to 20 ° C and diluted with water (10 ml).The layers were separated and the aqueous layer re-extracted with toluene (20 ml).The combined organic layers were washed with 20 ml of 5percent w / w aqueous NaCl and then with 10percent w / w NaCl (40 ml) and finally with 20 ml of water.The resulting toluene solution was treated with activated carbon.After filtration, the filtrate was concentrated to dryness to give an orange oil (14 g).Cyclohexane (12 ml) was added at -5 / -10 ° C and the resulting suspension was filtered and washed twice with 3.5 ml of cyclohexane.The solid was dried under vacuum in a 25 ° C oven to give 10.8 g of a white solidbody.The molar yield after separation was 75percent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4399 - 4403
[2]Patent: CN103992258,2017,B .Location in patent: Paragraph 0015; 0043; 0052-0061; 0064

2
[ 101385-93-7 ]
[ 109431-87-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With recombinant Chryseobacterium sp. CA 49 ketoreductase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; isopropyl alcohol; at 40℃; for 10h;pH 7.0;Enzymatic reaction;	General procedure: The reaction mixture containing 200 mM substrate, 1mM NAD+, 5% (v/v) 2-propanol and 10mg crude enzyme READH in 1mL potassium phosphate buffer (100mM, pH 7.0) was incubated at 50 C. For ChKRED20, 40% (v/v) 2-propanol and a reaction temperature of 40 C were applied instead. The reaction was monitored by TLC, and terminated by extracting with methyl tert-butyl ether (1 mL). The organic extract was dried over anhydrous sodium sulfate and concentrated. The samples were subjected to chiral HPLC to determine the conversion and enantiomeric excess. The products were purified by silica gel column chromatography, and identified by NMR analysis, optical rotation measurements and mass spectrometry.

Reference： [1]Process Biochemistry,2017,vol. 56,p. 90 - 97
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 2539 - 2549
[3]Journal of the American Chemical Society,2012,vol. 134,p. 18522 - 18525

3
[ 109431-87-0 ]
[ 101385-93-7 ]

Yield	Reaction Conditions	Operation in experiment
77.3%	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 0.2h;Inert atmosphere;	To a stirred solution of tert-butyl (R)-3-hydroxypyrrolidine-l-carboxylate (Intermediate 8-step 1, 4.5 g, 24.1 mmol) in DCM (60 ml) under N2atmosphere, was added DMP (20.45 g, 48.12 mmol) at 0 C. The reaction mixture was allowed to room temperature and stirred for about 2 hours. After completion of the reaction (monitored by TLC), the reaction mixture was quenched with 1 : 1 mixture of saturated NaHC03and saturated Na2S203solution. The reaction mixture was extracted with DCM (2x100 ml). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to give the residue. Purification by column chromatography with EtOAc and hexane (15:85) to afford the desired compound (3.44 g, yield: 77.3%) as an oil. 1H NMR (300 MHz, CDC13): δ 3.80-3.75 (m, 4H), 2.61-2.56 (m, 2H), 1.48 (s, 9H)
77.3%	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	To a stirred solution of tert-butyl (R)-3-hydroxypyrrolidine-1-carboxylate (4.5 g, 24.1 mmol) in DCM (60 ml) under N2 atmosphere, was added DMP (20.45 g, 48.12 mmol) at 0 C. The reaction mixture was allowed to room temperature and stirred for about 2 hours. After completion of the reaction (monitored by TLC), the reaction mixture was quenched with 1:1 mixture of saturated NaHCO3 and saturated Na2S2O3 solution. The reaction mixture was extracted with DCM (2*100 ml). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to give the residue. Purification by column chromatography with EtOAc and hexane (15:85) to afford the desired compound (3.44 g, yield: 77.3%) as an oil. 1H NMR (300 MHz, CDCl3): δ 3.80-3.75 (m, 4H), 2.61-2.56 (m, 2H), 1.48 (s, 9H).
34%	With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; at 20℃;	1) N-tert-Butoxycarbonyl-3-pyrrolidinone Pyridine-sulfur trioxide (4.12 g) was added to a solution of (3R)-N-tert-butoxycarbonyl-3-hydroxypyrrolidine (2.47 g) and triethylamine (9.19 mL) in dimethylsulfoxide (30 mL) at room temperature, and the resultant mixture was stirred overnight. The reaction solution was poured onto water and extracted with diethyl ether. The organic layer was washed with water and saturated saline, and then dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (ethyl acetate-hexane), to obtain N-tert-butoxycarbonyl-3-pyrrolidinone (855 mg, 34%) as an oily product. 1H-NMR (400MHz, CDCl3)δ: 1.47(9H, d, J=9.3Hz), 2.59(2H, t, J=7.8Hz), 3.75-3.80(4H, t, J=7.9Hz).

With sulfur trioxide trimethylamine complex; triethylamine; In dimethyl sulfoxide; at 20℃; for 18h;

(R)-pyrrolidinol (Tokyo Chemical Industry Co., Ltd., 12.4 g, 100 mmol) was dissolved in 100 ml of a 3 N aqueous solution of sodium hydroxide. A solution (50 ml) of di-tert-butyl dicarbonate (Tokyo Chemical Industry Co., Ltd., 25.0 g, 120 mmol) in tetrahydrofuran was added dropwise thereto at 0C. The pH value of the mixture was determined with a pH test paper and was found to be 11. The mixture was then stirred at room temperature for 2 hr and was then concentrated to remove a major part of tetrahydrofuran. The aqueous layer was extracted three times with ethylacetate. The combined organic layer was dried over sodium sulfate and was concentrated to give a crude product. The crude product and triethylamine (20 ml) were dissolved in anhydrous dimethylsulfoxide (100 ml), and a trituated sulfur trioxide/trimethylamine complex (Aldrich, 28.0 g, 200 mmol) was added little by little thereto at room temperature. The mixture was stirred at room temperature for 18 hr. Water (200 ml) was then added to the reaction solution to stop the reaction. The aqueous layer was extracted three times with ethylacetate. The combined organic layer was dried over sodium sulfate and was concentrated to give a crude product. The crude product was loaded on a silica gel column and developed with chloroform, followed by development with chloroform only to give an intermediate (11.25 g). The intermediate (3.70 g, 20 mmol) and 5-aminoisoquinoline (Aldrich, 2.48 g, 17 mmol) were dissolved in 100 ml of acetic acid. Sodium sulfate (14.2 g, 100 mmol) was added thereto, and the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0C, sodium hydride triacetate (Aldrich, 4.44 g, 20 mmol) was added thereto little by little, and the mixture was stirred at room temperature for 18 hr. The reaction solution was concentrated under the reduced pressure to remove a major part of acetic acid. The reaction mixture was then adjusted to pH = 8 by the addition of a saturated sodium hydrogencarbonate solution and was filtered through Celite, and the filtrate was separated into an organic layer and an aqueous layer. The aqueous layer was extracted three times with ethylacetate. The combined organic layer was dried over sodium sulfate and was concentrated to give a crude product. The crude product in methylene chloride was loaded on a silica gel column and developed with hexane. The development was first carried out with hexane only, subsequently with hexane/chloroform (1 : 1), and finally with chloroform only to collect a fraction having UV absorption with Rf = 0.6 to give the title compound (3.70 g, 12 mmol). 1H-NMR (CDCl3, 400 MHz): 1.46 (s, 9H), 1.75 - 1.94 (m, 1H), 2.02 - 2.10 (m, 1 H), 3.35 - 3.55 (m, 31 H), 3.75 - 3.86 (m, 1 H), 4.17 - 4.24 (m, 1 H), 4.705 - 4.90 (m, 1 H), 6.91 (d, J = 7.6 Hz, 1H), 7.44 (d, J = 8.3 Hz, 1 H), 7.58 (t, J = 7.9 Hz, 1 H), 7.80 - 7.90 (m, 1 H), 8.42 (d, J = 6.4 Hz, 1 H), 9.20 (s, 1 H). Mass spectrometric value (ESI-MS, m/z): 314 (M++1)

Reference： [1]Patent: WO2017/17630,2017,A1 .Location in patent: Page/Page column 56
[2]Patent: US2018/237472,2018,A1 .Location in patent: Paragraph 0166; 0167
[3]Patent: EP1785418,2007,A1 .Location in patent: Page/Page column 61-62
[4]Organic Process Research and Development,2017,vol. 21,p. 1419 - 1422
[5]Patent: EP1550660,2005,A1 .Location in patent: Page/Page column 9

4
[ 67-56-1 ]
[ 101385-93-7 ]
[ 149-73-5 ]
[ 1263283-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethyl acetate; for 8.5h;	To 3-oxo-pyrrolidine-1 -carboxylic acid tert- butyl ester (4.05 g) in 20 ml. of trimethylorthoformate was added 40 ml_ of a 4 N solution of HCI in methanol. The solution was stirred for 4.5 h, and the volume was reduced to ca 15 ml_ under vacuum. The solution was diluted with 60 ml_ of ethyl acetate and the mixture was stirred for 4 h. The resultant solids were collected via filtration to provide 2.97 g of the title compound as an off-white solid.

Reference： [1]Patent: WO2006/70284,2006,A1 .Location in patent: Page/Page column 39

5
[ 101385-93-7 ]
[ 845894-03-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: (+-)-N-BOC-trans-3-fluoro-4(methylamnino)pyrrolidine 2-3 A cooled solution (-78 C.) of N-BOC-3-pyrrolidinone (1.0 g, 5.41 mmol) in THF (50 mL) was treated with a solution of NaHMDS (7.03 mL of a 1M soln in THF). After stirring for 30 min, the solution was treated with chlorotriethylsilane (1.18 mL, 7.03 mmol). The reaction was stirred for 1 hr at -78 C., warmed to 0 C., diluted with 1:1 brine/water and hexanes. The mixture was extracted with EtOAc. The organic solution was dried over Na2SO4, filtered, and concentrated. The residue was not further purified. A solution of the 3-fluoro-N-BOC-pyrrolidinone (0.31 g, 1.53 mmol) in dichloroethane (10 mL) was treated with methylarnine (1.53 mL of a 2M soln in THF) and Na(OAc)3BH (0.49 g, 2.3 mmol). After stirring for 12 h at room temperature, the reaction was diluted with EtOAc and washed with satd NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2; 80% CHCl3/10% MeOH/10% EtOAc) to provide racemic 2-3. Data for 2-3: 1H-NMR (500 MHz, CDCl3) delta 5.11 (br d, J=55 Hz, 1H), 3.85-3.62 (m, 2H), 3.51 (m, 1H), 3.20 (m, 1H), 3.03 (m, 1H), 2.50 (s, 3H), 1.46 (s, 9H) ppm.

Reference： [1]Patent: US2006/287302,2006,A1 .Location in patent: Page/Page column 35-36

6
[ 14150-94-8 ]
[ 101385-93-7 ]
C₁₂H₁₅N₃O₄ [ No CAS ]
[ 1119103-44-4 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1932 - 1938

7
[ 38573-88-5 ]
[ 101385-93-7 ]
[ 1092573-65-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With n-hexyllithium; In diethyl ether; hexane; at -78 - 20℃;Inert atmosphere;	Preparation 10; TERT-BUTYL 3-(2,3-DIFLUOROPHENYL)-S-HYDROXYPYRROLIDINE-I - CARBOXYLATETo a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (8 g, 41.4 mmol) in dry diethyl ether (100 mL), under nitrogen, was added dropwise at -780C, n-hexyllithium (2.3 M in hexane, 18 ml, 41.4 mmol). The mixture was stirred for 1 min after which a solution of 1 -N-boc-3-pyrrolidone (7.66 g, 41.4 mmol) in dry diethyl ether (50 mL) was added dropwise. The resulting mixture was brought to ambient temperature and stirred for 2h, aqueous saturated ammonium chloride solution (50 ml) was added and the mixture was extracted with ethylacetate (2x50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography (ethylacetate/isooctane, 1 :9 to 1 :1 ) to give the title compound (8.12 g, 66percent). MS m/z (rel. intensity, 70 eV) 243 (26), 198 (48), 141 (33), 127 (38), 57 (bp).
66%		Preparation 10 TERT-BUTYL 3-(2,3-DIFLUOROPHENYL)-3-HYDROXYPYRROLIDINE-1 -CARBOXYLATETo a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (8 g, 41.4 mmol) in dry diethyl ether (100 mL), under nitrogen, was added dropwise at -78° C., n-hexyllithium (2.3 M in hexane, 18 ml, 41.4 mmol). The mixture was stirred for 1 min after which a solution of 1-N-boc-3-pyrrolidone (7.66 g, 41.4 mmol) in dry diethyl ether (50 mL) was added dropwise. The resulting mixture was brought to ambient temperature and stirred for 2h, aqueous saturated ammonium chloride solution (50 ml) was added and the mixture was extracted with ethylacetate (2x50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography (ethylacetate/isooctane, 1:9 to 1:1) to give the title compound (8.12 g, 66percent). MS m/z (rel. intensity, 70 eV) 243 (26), 198 (48), 141 (33), 127 (38), 57 (bp).
		MTBE (60 mL) was charged to a 3-neck round bottom flask followed by bromo-2,3- difluoro-benzene (12 mL, 107 mmol). The solution was cooled in ice/salt bath. When the internal temperature reached 40C addition of i-PrMgClLiCl solution in THF (1.3M, 90.7 mL, 118 mmol) was started. The higher internal temperature during addition was 2 °C(bath temperature was -8°C to -5°C); addition time 17 mm. After addition was complete the reaction mixture was stirred at -5°C to 0°C for one hour. Tert-Butyl 3-oxopyrrolidine-1 - carboxylate (21 .8 g, 118 mmol) solution in MTBE (200 mL) was added to the reaction mixture at -4°C to -2°C during 15 mm. under vigorous stirring. The reaction mixture was stirred at -2°C to 0°C for 3 hours and then quenched by addition of 20percent aqueousammonium chloride solution (260 mL). The internal temperature rose from 0 °C to 15 °C during addition. The cooling bath was removed and the mixture was stirred at room temperature for 1 hour. Layers were separated and the aqueous phase was re-extracted with MTBE (120 mL). Combined organic extracts were washed with brine (160 mL) and water (2 x 120 mL). Organic layer was concentrated to approx. 120 mL volume. MTBE(120 mL) was added and solvent evaporated to 120 mL volume left. 120 mL of MTBE was added again and evaporated till 120 mL volume left. Cyclohexane (120 mL) was added and mixture concentrated until remaining volume was 120 mL. Co-evaporation with cyclohexane was repeated two times using 120 mL of cyclohexane each time. Final solution (160 mL) was stirred at room temperature. After 30 minutes, solution becamecloudy and crystallization started. The slurry was stirred for 2 hours at room temperature and then for 2 hours at 5 to 10 °C. Precipitate was filtered off, washed on the filter with cyclohexane (2 x 30 mL). Since the freezing of cyclohexane causes suction to dry on the filter, wet material was dried under vacuum at 40 00. There was obtained 22 g (69percent) of the Compound of Formula (VIa) as a solid and the purity thereof was 98 areapercent as determined by HPLC (UV detection at 220 nm). Content of the impurity Compound of Formula (VIII) as described herein was 1 .2percent as determined by HPLC (UV detection at220 nm).

Reference： [1]Patent: WO2010/58018,2010,A1 .Location in patent: Page/Page column 31
[2]Patent: US2011/257241,2011,A1 .Location in patent: Page/Page column 13
[3]Patent: WO2018/211080,2018,A1 .Location in patent: Page/Page column 37

8
[ 7677-24-9 ]
[ 24424-99-5 ]
[ 101385-93-7 ]
[ 1067239-08-0 ]

Yield	Reaction Conditions	Operation in experiment
		General Procedure for Synthesis of q-hydroxy carboxylic acids. Step No. 1. O-(Trimethylsilyl) cyanohydrines: A 50-mL flask equipped with a magnetic stirring bar and drying tube was charged with the ketone or aldehyde (0.010 mmol), followed by THF (50 mL), trimethylsilyl cyanide (1.39 g, 14 mmol), and zinc iodide (0.090 g, 0.28 mmol), and the reaction mixture was stirred at room temperature for 24 hr. Solvent evaporation gave a residue, which was dissolved in EtOAc (60 mL), washed with 5% aq. NaHC03 (2 x 30 mL), H20 (30 mL), and brine (30 mL), dried over Na2S04, filtered and concentrated to dryness to yield a crude, which was carried through to the next step without further purification. Step No. 2. Acid hydrolysis to g-hydroxy carboxylic acid: AcOH (25 ml) and cone. HC1 (25 ml) were added to the unpurified material from step No.1 and the reaction mixture was refluxed for 2-3 hr. The reaction mixture was then concentrated to dryness to give a white solid, which was carried through to the next step without further purification.Step No. 3. Boc protection: To a stirring solution of solid from step No.2 in 2 M NaOH (20 mL) and i-PrOH (20 mL) at 0C was added Boc20 (6.6 g, 3 mmol) in small portions, and the reaction mixture was allowed to warm to room temperature over 4 h. i-PrOH was then evaporated, and H20 (50 mL) was added, and the aqueous phase was separated and extracted with Et20 (2 x 30 ml). The aqueous layer was acidified to pH 3 by addition of dilute H3P04 and was extracted with EtOAc (2 x 60 ml). The combined organic layers were washed with H20 (2 x 30 mL) and brine (30 mL), dried over Na2S04, filtered and concentrated to yield the desired N-Boc-a-hydroxy carboxylic acids in 56-72% yield.
		N-Boc-3-hydroxypyrrolidine-3-carboxylic acidN-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 15 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid; Procedure 15: General Procedure for Synthesis of alpha-hydroxy carboxylic acidsStep No. 1. O-(Trimethylsilyl) cvanohydrines: A 50-mL flask equipped with a magnetic stirring bar and drying tube was charged with the ketone or aldehyde (0.010 mmol), followed by THF (50 mL), trimethylsilyl cyanide (1.39 g, 14 mmol), and zinc iodide (0.090 g, 0.28 mmol), and the reaction mixture was stirred at room temperature for 24 hr. Solvent evaporation gave a residue, which was dissolved in EtOAc (60 niL), washed with 5% aq. NaHCO3 (2 x 30 mL), H2O (30 mL), and brine (30 mL), dried over Na2SO4, filtered and concentrated to dryness to yield a crude, which was carried through to the next step without further purification.Step No. 2. Acid hydrolysis to alpha-hydroxy carboxylic acid: AcOH (25 ml) and cone. HCl (25 ml) were added to the unpurified material from step No.1 and the reaction mixture was refluxed for 2-3 hr. The reaction mixture was then concentrated to dryness to give a white solid, which was carried through to the next step without further purification.Step No. 3. Boc protection: To a stirring solution of solid from step No.2 in 2 M NaOH (20 mL) and i-PrOH (20 mL) at 00C was added BoC2O (6.6 g, 3 mmol) in small portions, and the reaction mixture was allowed to warm to room temperature over 4 h. i-PrOH was then evaporated, and H2O (50 mL) was added, and the aqueous phase was separated and extracted with Et2O (2 x 30 ml). The aqueous layer was acidified to pH 3 by addition of dilute H3PO4 and was extracted with EtOAc (2 x 60 ml). The combined organic layers were washed with H2O (2 x 30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated to yield the desired N-Boc-alpha-hydroxy carboxylic acids in 56-72% yield. Aldehydes and ketones used: N-Boc-3-Pyrrolidonone, N-Boc-3- azetidinone, N-Boc-4-piperidone and N-Boc-3-azetidincarboxaldehyde.

Reference： [1]Patent: WO2011/44498,2011,A1 .Location in patent: Page/Page column 64-65, 72
[2]Patent: WO2010/132777,2010,A2 .Location in patent: Page/Page column 46-47; 152-153

9
[ 15861-23-1 ]
[ 101385-93-7 ]
[ 1360095-67-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (1 10 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.1 1 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.
		Intermediate 10tert-butyl 3-(5-cyanoindolin-l-yl)pyrrolidine-l-carboxylate[0109] To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaC BH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.
		tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-1-carboxylate (166 mg, 0.90 mmol) and HOAc (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

Reference： [1]Patent: WO2012/22265,2012,A1 .Location in patent: Page/Page column 34
[2]Patent: WO2012/22045,2012,A1 .Location in patent: Page/Page column 29-30
[3]Patent: US2013/210831,2013,A1 .Location in patent: Paragraph 0212

10
[ 541-41-3 ]
[ 101385-93-7 ]
[ 146256-98-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5℃; for 2.66667h;	1000ml four-necked flask by adding Boc-pyrrolidone 120g, DMF 600ml, Stirring down to 0-5 , Sodium hydride was added to 26 g, 70.5 g of ethyl chloroformate was slowly added dropwise with stirring, 40min drop finished. 0-5 reaction 2h, TLC detection reaction is completed, Slowly add 3L ice water, With dilute hydrochloric acid to adjust the pH = 7 after ethyl acetate extraction, dry, Concentrated to give intermediate 1. Yield 85percent.

Reference： [1]Patent: CN106905325,2017,A .Location in patent: Paragraph 0030-0032

11
[ 38573-88-5 ]
[ 101385-93-7 ]
[ 1227638-67-6 ]

Reference： [1]Patent: WO2018/211080,2018,A1

12
[ 129488-10-4 ]
[ 101385-93-7 ]
C₂₁H₃₀N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.7%		Compound TDI01209-1 (1.0 g, 4.3 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (800 mg, 4.3 mmol), 1,2-dichloroethane (30 mL) and glacial acetic acid (8 drops) were added to a 50 mL single neck flask, and the reaction wasperformed at room temperature (15?25°C) for 1.5 h. Sodium triacetoxyborohyride (2.73 g, 12.9 mmol) was then added,and the reaction was performed at 50°C for 2 h. The reaction solution was added with 40 mL water, and extracted withdichloromethane (15 mL * 2). The organic phase was combined, washed with saturated brine, dried over anhydroussodium sulfate, and purified by column chromatography (petroleum ether : ethyl acetate=10:1-7:1) to afford TDI01209-2(1.44 g, light yellow solid, yield: 83.7percent).1H NMR (400 MHz, CDCl3) delta 8.04 - 7.94 (m, 2H), 6.88 (dd, J = 8.9, 2.1 Hz, 1H), 6.78 (d, J = 1.9 Hz, 1H), 3.47 (s, 4H),2.22 (s, 1H), 1.95 (d, J = 9.0 Hz, 1H), 1.71 (s, 9H), 1.46 (s, 10H), 1.26 (t, J = 7.1 Hz, 1H). MS m/z (ESI): 403.2 [M+H].
83.7%		Compound TDI01209-1 (1.0 g, 4.3 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (800 mg, 4.3 mmol), 1,2-dichloroethane (30 mL) and glacial acetic acid (8 drops) were added to a 50 mL single neck flask, and the reaction was performed at room temperature (15?25°C) for 1.5 h. Sodium triacetoxyborohyride (2.73 g, 12.9 mmol) was then added, and the reaction was performed at 50°C for 2 h. The reaction solution was added with 40 mL water, and extracted with dichloromethane (15 mL * 2). The organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography (petroleum ether : ethyl acetate=10:1-7:1) to afford TDI01209-2 (1.44 g, light yellow solid, yield: 83.7percent). 1H NMR (400 MHz, CDCl3) delta 8.04 - 7.94 (m, 2H), 6.88 (dd, J = 8.9, 2.1 Hz, 1H), 6.78 (d, J = 1.9 Hz, 1H), 3.47 (s, 4H), 2.22 (s, 1H), 1.95 (d, J = 9.0 Hz, 1H), 1.71 (s, 9H), 1.46 (s, 10H), 1.26 (t, J = 7.1 Hz, 1H). MS m/z (ESI): 403.2 [M+H].

Reference： [1]Patent: EP3421465,2019,A1 .Location in patent: Paragraph 0198; 0199
[2]Patent: EP3421464,2019,A1 .Location in patent: Paragraph 0164; 0165

13
[ 14704-31-5 ]
[ 101385-93-7 ]
tert-butyl 2-(biphenyl-3-ylmethyl)-3-oxopyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.92 g		To a mixture of tert-butyl 3-oxopyrrolidine-l-carboxylate (3.5 g) and toluene (30 mL) was added pyrrolidine (1.61 g) at room temperature. The mixture was stirred at 100C for 3 hr, and concentrated. CH3CN (30 mL) and 3- (bromomethyl ) biphenyl (4.67 g) were added thereto at room temperature. The mixture was stirred overnight under nitrogen atmosphere at 80C, and concentrated. The obtained residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.92 g) . MS: [M+H-Boc]+ 252.2.

Reference： [1]Patent: WO2019/27058,2019,A1 .Location in patent: Paragraph 0269

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Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 101385-93-7 ] {[proInfo.proName]}

Quality Control of [ 101385-93-7 ]

Related Doc. of [ 101385-93-7 ]

Product Details of [ 101385-93-7 ]

Calculated chemistry of [ 101385-93-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 101385-93-7 ]

Application In Synthesis of [ 101385-93-7 ]

[ 101385-93-7 ] Synthesis Path-Upstream 1~6

[ 101385-93-7 ] Synthesis Path-Downstream 1~13

Technical Information

Related Functional Groups of [ 101385-93-7 ]

Amides

Ketones

Related Parent Nucleus of [ 101385-93-7 ]

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 101385-93-7 ]

Related Parent Nucleus of
[ 101385-93-7 ]