[ CAS No. 34368-52-0 ] {[proInfo.proName]}

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Quality Control of [ 34368-52-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 34368-52-0 ]

SDS Specification

Alternatived Products of [ 34368-52-0 ]

Product Details of [ 34368-52-0 ]

CAS No. :	34368-52-0	MDL No. :	MFCD06796625
Formula :	C₄H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	101.10	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 34368-52-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	27.31
TPSA :	49.33 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.82
Log Po/w (XLOGP3) :	-0.95
Log Po/w (WLOGP) :	-1.51
Log Po/w (MLOGP) :	-1.19
Log Po/w (SILICOS-IT) :	0.16
Consensus Log Po/w :	-0.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.13
Solubility :	137.0 mg/ml ; 1.35 mol/l
Class :	Highly soluble
Log S (Ali) :	0.4
Solubility :	253.0 mg/ml ; 2.5 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.05
Solubility :	90.7 mg/ml ; 0.897 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 34368-52-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 34368-52-0 ]

* 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 [ 34368-52-0 ]
Downstream synthetic route of [ 34368-52-0 ]

[ 34368-52-0 ] Synthesis Path-Upstream 1~5

1
[ 3938-83-8 ]
[ 34368-52-0 ]

Yield	Reaction Conditions	Operation in experiment
12.9%	With aluminum oxide In toluene for 19 h; Reflux; Dean-Stark	Compound 27: Compound 1 (l .Og, 8.40 mmol ) and alumina (2.57g, 25.20 mmol) were suspended in toluene (43 mL) and heated to reflux with attached Dean- Stark apparatus. The reaction was allowed to proceed at reflux for 19 hours. The reaction was filtered and the solid washed with CH2CI2. The filtrate was then collected and concentrated to yield compound 27 as colorless crystals (0.1 10 g, 12.9percent). Using FI RM S analysis, the composition of compound 27 was determined to be CiH NChNa. Measured mass was 124.0371 ; theoretical mass was 124.0369. NMR analysis results for compound 27 were NMR (600 MHz, CDC I3) δ 7.63 (bs, I H), 5.35 (d, J 5.4 Hz, 1H), 4.02-3.95 (m, I H), 3.18-3.12 (m, 1H), 3. 1 I - 3.04 (m, I H), 2.28-2.21 (m, IH), 1.79- 1.69 (m, I H). ¹³C NMR (151 MHz, CDCI3) δ 176.7, 68.4, 37.5, 30.5.

Reference： [1] Synlett, 2008, # 13, p. 2028 - 2032
[2] Journal of the American Chemical Society, 2000, vol. 122, # 2, p. 408 - 409
[3] Patent: WO2016/164828, 2016, A1, . Location in patent: Page/Page column 26
[4] Bulletin de la Societe Chimique de France, 1987, # 2, p. 297 - 301
[5] Journal of the Chemical Society, Chemical Communications, 1995, # 2, p. 231 - 232
[6] Patent: WO2011/13141, 2011, A2, . Location in patent: Page/Page column 50; 51
[7] Patent: US2012/184544, 2012, A1, . Location in patent: Page/Page column 24
[8] Patent: WO2014/8285, 2014, A1, . Location in patent: Page/Page column 165
[9] Journal of Organic Chemistry, 2018, vol. 83, # 13, p. 7085 - 7101

2
[ 630127-11-6 ]
[ 34368-52-0 ]

Reference： [1] Heterocycles, 2003, vol. 60, # 8, p. 1833 - 1841

3
[ 194034-36-1 ]
[ 34368-52-0 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 27, p. 9213 - 9218

4
[ 194034-43-0 ]
[ 34368-52-0 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 27, p. 9213 - 9218

5
[ 111466-53-6 ]
[ 34368-52-0 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1987, # 2, p. 297 - 301

[ 34368-52-0 ] Synthesis Path-Downstream 1~10

1
[ 3938-83-8 ]
[ 34368-52-0 ]

Yield	Reaction Conditions	Operation in experiment
12.9%	With aluminum oxide; In toluene; for 19h;Reflux; Dean-Stark;	Compound 27: Compound 1 (l .Og, 8.40 mmol ) and alumina (2.57g, 25.20 mmol) were suspended in toluene (43 mL) and heated to reflux with attached Dean- Stark apparatus. The reaction was allowed to proceed at reflux for 19 hours. The reaction was filtered and the solid washed with CH2CI2. The filtrate was then collected and concentrated to yield compound 27 as colorless crystals (0.1 10 g, 12.9%). Using FI RM S analysis, the composition of compound 27 was determined to be CiH NChNa. Measured mass was 124.0371 ; theoretical mass was 124.0369. NMR analysis results for compound 27 were NMR (600 MHz, CDC I3) delta 7.63 (bs, I H), 5.35 (d, J 5.4 Hz, 1H), 4.02-3.95 (m, I H), 3.18-3.12 (m, 1H), 3. 1 I - 3.04 (m, I H), 2.28-2.21 (m, IH), 1.79- 1.69 (m, I H). 13C NMR (151 MHz, CDCI3) delta 176.7, 68.4, 37.5, 30.5.
		Cone. H2SO4 (14.8 g, 8 mL) was added drop wise over 5 min to the stirring solution of (5)-(-)-4-Amino-2-hydroxybutyric acid (15 g) [CAS No. 40371-51-5] in MeOH (95 rnL) under dry conditions using anhydrous CaCl2 guard tube. After refluxing for 4 h, the reaction mixture was allowed to cool to room temperature and diluted with water (15 mL). Potassium carbonate (24 g) was added in portions to the reaction mixture and stirred overnight (20 h). Reaction mixture was diluted with CHCl3, filtered through celite. Celite bed was thoroughly washed with 1 % MeOHiCHCl3. The filtrates were combined and evaporated to dryness to obtain thick liquid residue. The residue was subjected to aging using 1-2 % MeOHiCHCl3 and then filtered. Organic layers were combined, dried over anhydrous sodium sulphate, filtered and concentrated to obtain the white solid. (1 1.8 g)1H NMR (CDCl3, 400 MHz) delta ppm: 2.03-2.13 (m, 1 H), 2.48-2.55 (m, 1 H), 3.30-3.35(m, IH), 3.36-3.50 (m, 1 H), 4.34 (t, J = 8.4 Hz, 1 H), 6.51 (bs, 1 H); [alpha]D25: + 98, c =1, CHCl3
		(S)-(-)-3-hydroxy-2-pyrrolidinone Conc. H2SO4 (14.8 g, 8 mL) was added drop wise over 5 min to the stirring solution of (S)-(-)-4-Amino-2-hydroxybutyric acid (15 g) [CAS No. 40371-51-5] in MeOH (95 mL) under dry conditions using anhydrous CaCl2 guard tube. After refluxing for 4 h, the reaction mixture was allowed to cool to room temperature and diluted with water (15 mL). Potassium carbonate (24 g) was added in portions to the reaction mixture and stirred overnight (20 h). Reaction mixture was diluted with CHCl3, filtered through celite. Celite bed was thoroughly washed with 1% MeOH:CHCl3. The filtrates were combined and evaporated to dryness to obtain thick liquid residue. The residue was subjected to aging using 1-2% MeOH:CHCl3 and then filtered. Organic layers were combined, dried over anhydrous sodium sulphate, filtered and concentrated to obtain the white solid. (11.8 g) 1H NMR (CDCl3, 400 MHz) delta ppm: 2.03-2.13 (m, 1H), 2.48-2.55 (m, 1H), 3.30=3.35 (m, 1H), 3.36-3.50 (m, 1H), 4.34 (t, J=8.4 Hz, 1H), 6.51 (bs, 1H); [alpha]D25: +98, c=1, CHCl3

With sulfuric acid; In methanol; water; for 18h;Reflux;

Step 1. Preparation of 018-1: (Prepared according to W0201 1013141) Toa solution of (S)-4-amino-2-hydroxybutanoic acid (15 g, 126 mmol) in methanol(95 mL) was added concentrated sulfuric acid (8 mL), and the reaction washeated to reflux. After 18 h, the resulting mixture was allowed to cool to roomtemperature and was concentrated in vacuo. The residue was slurried with ethylacetate (95 mL) and 018-1 was collected by vacuum filtration. 1H NMR (400MHz, ODd3) 6 5.69 (br s, 1 H), 4.31 (ddd, J = 9.2, 8.1, 2.2 Hz, 1 H), 3.49 (d, J = 5.6 Hz, 1 H), 3.41 (tt, J = 9.2, 1 .7 Hz, 1 H), 3.33 (td, J = 9.4, 6.5 Hz, 1 H), 2.81 (br s, 1H), 2.59-2.48 (m, 1H), 2.09 (dq, J= 12.9, 9.1 Hz, 1H).

Reference： [1]Synlett,2008,p. 2028 - 2032
[2]Journal of the American Chemical Society,2000,vol. 122,p. 408 - 409
[3]Patent: WO2016/164828,2016,A1 .Location in patent: Page/Page column 26
[4]Bulletin de la Societe Chimique de France,1987,p. 297 - 301
[5]Journal of the Chemical Society. Chemical communications,1995,p. 231 - 232
[6]Patent: WO2011/13141,2011,A2 .Location in patent: Page/Page column 50; 51
[7]Patent: US2012/184544,2012,A1 .Location in patent: Page/Page column 24
[8]Patent: WO2014/8285,2014,A1 .Location in patent: Page/Page column 165
[9]Journal of Organic Chemistry,2018,vol. 83,p. 7085 - 7101

2
[ 34368-52-0 ]
[ 109-92-2 ]
[ 881830-67-7 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2587 - 2593

3
[ 332133-82-1 ]
[ 34368-52-0 ]
[ 332135-05-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; copper(I) iodide; potassium carbonate; In 1-methyl-pyrrolidin-2-one; ethyl acetate;	a 2-Benzyl-3-methoxymethyloxy-6-[<strong>[34368-52-0](3S)-3-hydroxy-2-pyrrolidinone</strong>-1-yl]pyridine 14.3 g of 2-benzyl-3-methoxymethyloxy-6-iodopyridine (Production Example 12) and 4.1 g of <strong>[34368-52-0](3S)-3-hydroxy-2-pyrrolidinone</strong> synthesised according to a method well-known in a literature (Synthesis, 1978, 614), 4.6 g of cuprous iodide and 13.7 g of potassium carbonate were suspended in 30 ml of 1-methyl-2-pyrrolidinone, followed by heating under stirring at 140 C. in an oil bath for 20 minutes in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto. The mixture was extracted with ethyl acetate, and the organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 50-60% ethyl acetate as an eluent for separation and purification, to give 9.7 g of the target compound. 1H-NMR (CDCl3) delta=1.95-2.08 (1H, m), 2.53-2.58 (1H, m), 3.09 (1H, br.s), 3.37 (3H, s), 3.76 (1H, td, J=10 Hz, 6.6 Hz), 4.12 (2H, s), 4.19 (1H, t, J=9.2 Hz), 4.48 (1H, t, J=10 Hz), 5.14 (2H, s), 7.17-7.30 (5H, m), 7.42 (1H, d, J=9.0 Hz), 8.14 (1H, d, J=9.0 Hz).

Reference： [1]Patent: US6599917,2003,B1

4
[ 34368-52-0 ]
(S)-3-acetoxy-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In pyridine;	(1) To a solution of 1.439 g of (S)-(-)-3-hydroxy-2-pyrrolidinone [P. W. K. Woo, Tetrahedron Letters, 2617 (1971); mp. 103.5°-104.5° C., [alpha]D26 =-118.8°+-2.3° (c=0.688, CHCl3)] in 14 ml of pyridine is added 2.8 ml of acetic anhydride, and the mixture is allowed to stand at room temperature for 4 hours and concentrated under reduced pressure at a temperature below 40° C. The residue is crystallized from ether and recrystallized from methylene chloride-n-hexane to give 1.735 g of (S)-(-)-3-acetoxy-2-pyrrolidinone in 86.3percent yield. mp. 85.5°-87° C. [alpha]D26 =-40.1°+-0.8° (c=1.015, CHCl3) Elemental Analysis (for C6 H9 NO3) Calcd (percent): C, 50.35; H, 6.29; N, 9.79. Found (percent): C, 50.50; H, 6.36; N, 9.66. IR: numaxNujol 3170, 3135, 1742, 1715, 1692 cm-1.

Reference： [1]Patent: US4248865,1981,A

5
methane sulphonyl chloride [ No CAS ]
[ 34368-52-0 ]
[ 115538-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; acetone;	EXAMPLE 2 (S)-3-Methanesulfonyloxy-Pyrrolidin-2-One Suspend the product of Example 1 (8 g., 79.2 mmol.) in dry methylene chloride (30 ml.) and cool to 0 C. Treat the suspension sequentially with dry triethylamine (16 ml., 118.8 mmol.) and methane sulfonyl chloride (6.74 ml., 87.12 mmol.). Stir at 5-10 C. for 1.5 hours, and subject the mixture to flash chromatography using acetone (5-10%) in dichloromethane to yield the title compound as a white solid. Optical rotation: [alpha]D26 =-68.3 (C=0.62, CHCl3) M.P.: 122-124 C. 200 MHz NMR(CDCl3): delta2.45(m,2H), 3.20(s,3H), 3.35(m,2H), 5.10(t,J=8 Hz,1H) and 7.75(br-S,1H-NH). MS: 180(M+1).

Reference： [1]Patent: US4762827,1988,A

6
[ 34368-52-0 ]
[ 307316-12-7 ]

Yield	Reaction Conditions	Operation in experiment
77.5%	With pyridine; thionyl chloride; sodium chloride; In 1,4-dioxane; water; ethyl acetate;	Example 1 [Compound (1) --> (2)] <strong>[34368-52-0](S)-3-Hydroxy-2-pyrrolidinone</strong> (100.4 mg) was dissolved in 3 ml of dioxane, 248.4 mg of thionyl chloride was added, and the mixture was stirred at room temperature for 4 hours. Further, 3.0 mg of pyridine was added, and the mixture was stirred at 50°C for 3 hours. After confirmation of disappearance of the starting material by TLC, the reaction solvent was distilled off under reduced pressure and, then, water and ethyl acetate were added. The aqueous layer was extracted five times with ethyl acetate. All the organic layers were combined and washed with a saturated aqueous solution of sodium chloride. After drying over sodium sulfate, the solvent was distilled off to give 92.0 mg of (R)-3-chloro-2-pyrrolidinone (yield 77.5percent, optical purity 93.5percent ee). For the analysis of the optical purity, high performance liquid chromatography using a chiral column (Chiralcel OB-H (Daicel)) was used. 1H-NMR (D2O) delta 2.35 (m, 1H), 2.74 (m, 1H), 3.46 (m, 1H), 3.54 (m, 1H), 4.58 (t, 1H) 13C-NMR (D2O) delta 34.2, 43.2, 58.0, 179.1 IR (KBr) 1700 cm-1
	With pyridine; thionyl chloride; In dichloromethane; at 10℃; for 3h;	To a 10 °C solution of <strong>[34368-52-0](S)-3-hydroxypyrrolidin-2-one</strong> (120 g, 1 .19 mol) in pyridine (38.4 ml, 475 mmol) and dichloromethane (3 L) at 10 °C was added thionyl chloride (173 ml, 2.37 mol) dropwise and the reaction was stirred for an additional 3 h. The reaction was concentrated in vacuo, taken up in dichloromethane and purified by filtering through a plug of silica gel, eluting with 10 L ethyl acetate. The material was concentrated in vacuo to approximately 1 L, diluted with 1 .5 L diethyl ether and heated gently for 15 min. The suspension was filtered, washed with diethyl ether (500 ml_), dried in vacuo, taken up in diethyl ether (1 L) and heated at 45 °C then filtered to afford 105 g of the title compound as a white solid.

Reference： [1]Patent: EP1193253,2002,A1
[2]Patent: WO2013/8217,2013,A1 .Location in patent: Page/Page column 42

7
[ 34368-52-0 ]
[ 100243-39-8 ]

Yield	Reaction Conditions	Operation in experiment
		(S)-3-Hydroxy-2-pyrrolidineon 9 (0.1 mol, 10.11 g), diglym (1.13 mol, 151.65 g) and NaBH (0.4 mol, 15.13 g) were added to a 500D round-bottom flask at 25oC°C, and sulfuric acid (20.2 g) was gently dropped thereto for 1 hour. After the dropping, the mixture was heated to 8O0C and kept for 12 hours to complete the reaction. When the reaction was completed, methanol was added thereto to inactivate the reaction, and the reaction mixture was neutralized with diluted hydrochloric acid (0.4 mol, 41.67 g). Then, pH of the reaction mixture was adjusted to 11 or more by using an aqueous sol ution of sodium hydroxide (ION 35D), and salts precipitated therefrom were removed through filtration. A resulting filtrate was concentrated under reduced pressure to obtain a (S)-3-hydroxypyrrolidine 1 residue. The residue was distilled under reduced pressure to obtain pure (S)-3-hydroxypyrrolidine 1.[122] 1H-NMR (CDCl ): delta 4.3-4.4 (m, IH), 3.05-3.15 (m, IH), 3.0 (bs, 2H), 2.75-2.9 (m,3H), 1.85-2.0 (m, IH), 1.6-1.75 (m, IH). EPO <DP n="15"/>[123] [124]
		EXAMPLE 9 Preparation of (S)-3-hydroxypyrrolidine 1 (S)-3-Hydroxy-2-pyrrolidineon 9 (0.1 mol, 10.11 g), diglym (1.13 mol, 151.65 g) and NaBH (0.4 mol, 15.13 g) were added to a 500.box. round-bottom flask at 25oC° C., and sulfuric acid (20.2 g) was gently dropped thereto for 1 hour. After the dropping, the mixture was heated to 80° C. and kept for 12 hours to complete the reaction. When the reaction was completed, methanol was added thereto to inactivate the reaction, and the reaction mixture was neutralized with diluted hydrochloric acid (0.4 mol, 41.67 g). Then, pH of the reaction mixture was adjusted to 11 or more by using an aqueous solution of sodium hydroxide (10N 35.box.), and salts precipitated therefrom were removed through filtration. A resulting filtrate was concentrated under reduced pressure to obtain a (S)-3-hydroxypyrrolidine 1 residue. The residue was distilled under reduced pressure to obtain pure (S)-3-hydroxypyrrolidine 1. 1H-NMR (CDCl3): delta 4.3-4.4 (m, 1H), 3.05-3.15 (m, 1H), 3.0 (bs, 2H), 2.75-2.9 (m, 3H), 1.85-2.0 (m, 1H), 1.6-1.75 (m, 1H).

Reference： [1]Patent: WO2007/11162,2007,A1 .Location in patent: Page/Page column 13
[2]Patent: US2008/214837,2008,A1 .Location in patent: Page/Page column 6
[3]Advanced Synthesis and Catalysis,2013,vol. 355,p. 47 - 52

8
4-amino-(S)-2-hydroxybutylic acid methylester sulfonate [ No CAS ]
[ 34368-52-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate; In water; at 20℃; for 12h;	After the reaction mixture was cooled down to room temperature, water (11.91 g) and potassium carbonate were added thereto and agitated at room temperature for 12 hours to obtain (S)-3-hydroxy-2-pyrrolidineon. At this time, the formation of (S)-3-hydroxy-2-pyrrolidineon was confirmed by NMR. Inorganic substances, which were precipitated by adding methanol to a residue obtained after filtering and concentrating the reaction mixture, were removed by filtering the reaction mixture twice, and a filtrate thus obtained was concentrated under reduced pressure to obtain (S)-3-hydroxy-2-pyrrolidineon 9 (yield: 89percent).[118] 1H-NMR (DMSO-d ): delta 7.6 (bs, IH), 5.4 (bs, IH), 3.97 (t, IH, J = 8.4 Hz), 3.0-3.2(m, 2H), 2.2-2.3 (m, IH), 1.6-1.8 (m, IH).
	With potassium carbonate; In methanol; water; at 20℃; for 12h;	EXAMPLE 8Preparation of (S)-3-hydroxy-2-pyrrolidineon 9After 4-amino-(S)-2-hydroxybutylic acid 2 (0.1 mol, 11.91 g) was dissolved in a solvent of methanol (1.5 mol, 48.06 g) contained in a 500 round-bottom flask, sulfuric acid (1 to 2 equivalents) was added thereto at 25° C. When 4-amino-(S)-2-hydroxybutylic acid 2 was completely dissolved, the reaction mixture was heated to 80° C. and agitated under reflux for 4 hours to complete the reaction. Thereafter, 4-amino-(S)-2-hydroxybutylic acid methylester sulfonate 8 was confirmed by NMR.1H-NMR (D2O): delta 4.46 (dd, 1H, J=8.4 Hz, 4.2 Hz), 3.78 (s, 3H), 3.17 (t, 2H, J=7.2 Hz), 2.18-2.35 (m, 1H), 1.95-2.13 (m, 1H).After the reaction mixture was cooled down to room temperature, water (11.91 g) and potassium carbonate were added thereto and agitated at room temperature for 12 hours to obtain (S)-3-hydroxy-2-pyrrolidineon. At this time, the formation of (S)-3-hydroxy-2-pyrrolidineon was confirmed by NMR. Inorganic substances, which were precipitated by adding methanol to a residue obtained after filtering and concentrating the reaction mixture, were removed by filtering the reaction mixture twice, and a filtrate thus obtained was concentrated under reduced pressure to obtain (S)-3-hydroxy-2-pyrrolidineon 9 (yield: 89percent).1H-NMR (DMSO-d6): delta 7.6 (bs, 1H), 5.4 (bs, 1H), 3.97 (t, 1H, J=8.4 Hz), 3.0-3.2 (m, 2H), 2.2-2.3 (m, 1H), 1.6-1.8 (m, 1H).

Reference： [1]Patent: WO2007/11162,2007,A1 .Location in patent: Page/Page column 9; 13
[2]Patent: US2008/214837,2008,A1 .Location in patent: Page/Page column 6

9
[ 34368-52-0 ]
[ 13154-24-0 ]
(S)-3-(triisopropylsiloxy)-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃;	1-79: to a solution of fSj-3 -hydroxypyrrol i di none (488 mg, 4.83 mmol) in DMF (10 mL), was added imidazole (493 mg, 1.5 equiv.), followed by triisopropyl silyl chloride (1.12 g, 1.2 equiv.). The reaction mixture was stirred at ambient temperature. On completion of the reaction, the reaction mixture was diluted with EtOAc (100 mL) and washed with H20 (5 x 20 mL). The aqueous washes were combined and back-extracted with EtOAc (50 mL). The combined organic extracts were washed with brine (50 mL), dried (MgS04) and concentrated to afford a colorless oil. Purification by silica gel chromatography (12 g pre-packed column, eluting with 35-60% EtOAc in Hexanes) afforded 1.23 g (99% yield) of the TIPS -protected alcohol as a colorless oil.
	With dmap; triethylamine; In dichloromethane; for 72h;	In step 3-1, triethylamine (20 ml ,139 mmol), p-N,N-dimethylaminopyridine (150 mg, 1 mmol) and then triisopropylsilyl chloride (22.6 grams, 118 mmol) were added dropwise over 4 minutes to a solution of iotaS'-3-hydroxy-2-pyrrolidinone (4.00 grams, 39.6 mmol) in 40 mL of methylene chloride. The reaction mixture was stirred for 3 days and was then quenched with 200 mL of brine. The solution was extracted with of ethyl acetate (3 x 300 mL) and the organic extracts were concentrated using a rotary evaporator. The product was then used directly without any purification.

Reference： [1]Patent: WO2019/183577,2019,A1 .Location in patent: Page/Page column 162; 163
[2]Organic Letters,2016,vol. 18,p. 2552 - 2555
[3]Journal of Organic Chemistry,2018,vol. 83,p. 7085 - 7101
[4]Patent: WO2009/140128,2009,A2 .Location in patent: Page/Page column 108

10
[ 34368-52-0 ]
[ 100-39-0 ]
[ 1228468-93-6 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 3037 - 3040

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Isomers

Technical Information

? Acyl Group Substitution ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Jones Oxidation ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 34368-52-0 ]

Alcohols

[ 77510-50-0 ]

(R)-3-Hydroxypyrrolidin-2-one

Similarity: 1.00

[ 15166-68-4 ]

3-Hydroxy-2-pyrrolidinone

Similarity: 1.00

[ 25747-41-5 ]

4-Hydroxy-2-pyrrolidone

Similarity: 0.89

[ 68108-18-9 ]

(S)-4-Hydroxypyrrolidine-2-one

Similarity: 0.89

[ 22677-21-0 ]

(R)-4-Hydroxypyrrolidin-2-one

Similarity: 0.89

Amides

[ 77510-50-0 ]

(R)-3-Hydroxypyrrolidin-2-one

Similarity: 1.00

[ 15166-68-4 ]

3-Hydroxy-2-pyrrolidinone

Similarity: 1.00

[ 25747-41-5 ]

4-Hydroxy-2-pyrrolidone

Similarity: 0.89

[ 68108-18-9 ]

(S)-4-Hydroxypyrrolidine-2-one

Similarity: 0.89

[ 22677-21-0 ]

(R)-4-Hydroxypyrrolidin-2-one

Similarity: 0.89

Related Parent Nucleus of
[ 34368-52-0 ]

Pyrrolidines

[ 77510-50-0 ]

(R)-3-Hydroxypyrrolidin-2-one

Similarity: 1.00

[ 15166-68-4 ]

3-Hydroxy-2-pyrrolidinone

Similarity: 1.00

[ 25747-41-5 ]

4-Hydroxy-2-pyrrolidone

Similarity: 0.89

[ 68108-18-9 ]

(S)-4-Hydroxypyrrolidine-2-one

Similarity: 0.89

[ 22677-21-0 ]

(R)-4-Hydroxypyrrolidin-2-one

Similarity: 0.89

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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. 34368-52-0 ] {[proInfo.proName]}

Quality Control of [ 34368-52-0 ]

Related Doc. of [ 34368-52-0 ]

Product Details of [ 34368-52-0 ]

Calculated chemistry of [ 34368-52-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 34368-52-0 ]

Application In Synthesis of [ 34368-52-0 ]

[ 34368-52-0 ] Synthesis Path-Upstream 1~5

[ 34368-52-0 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 34368-52-0 ]

Alcohols

Amides

Related Parent Nucleus of [ 34368-52-0 ]

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 34368-52-0 ]

Related Parent Nucleus of
[ 34368-52-0 ]