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[ CAS No. 392331-66-7 ] {[proInfo.proName]}

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Chemical Structure| 392331-66-7
Chemical Structure| 392331-66-7
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Quality Control of [ 392331-66-7 ]

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Product Details of [ 392331-66-7 ]

CAS No. :392331-66-7 MDL No. :MFCD11579803
Formula : C11H22N2O3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :XYWCDAFPRBDRER-UHFFFAOYSA-N
M.W : 230.30 Pubchem ID :23396319
Synonyms :

Calculated chemistry of [ 392331-66-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.31
TPSA : 75.79 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : -0.14
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : 0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.92
Solubility : 28.0 mg/ml ; 0.121 mol/l
Class : Very soluble
Log S (Ali) : -1.0
Solubility : 23.2 mg/ml ; 0.101 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.97
Solubility : 24.6 mg/ml ; 0.107 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 392331-66-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 392331-66-7 ]

* 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.

  • Downstream synthetic route of [ 392331-66-7 ]

[ 392331-66-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 147804-30-6 ]
  • [ 392331-66-7 ]
YieldReaction ConditionsOperation in experiment
95% With ammonium hydroxide; In methanol; at 80℃; for 16h;Sealed tube; A 100-mL sealed tube fitted with a magnetic stir bar was charged with tert-Butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (300 mg, 1.28 mmol) and a solution of ammonium hydroxide in methanol (20 mL, 7M). The solution was stirred for 16 h at 80 C. in an oil bath and cooled to room temperature. The mixture was concentrated under vacuum to afford tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate (350 mg, >95%) used without further purification. LCMS (ESI) m/z 231 [M+H].
86% With ammonia; In methanol; at 20℃; for 12h; To a stirred solution of tert-butyl 1-oxa-6-aza-spiro[2.5]octane-6-carboxylate (0.64 grams, 3.0 mmol, obtained in the above step) in methanol (4 mL) at room temperature, a solution of ammonia (NH3) in methanol (7M, 8 mL) was added and the reaction was stirred for12 hours. The volatiles were removed under reduced pressure to obtain the crude mass which was triturated with hexanes and ether which yielded the above titled compound (0.6 gram). Yield: 86 %.?H - NMR CDCI3 (6 ppm): 1.45 (9H, s), 1.35 - 1.60 (4H, m), 2.63 (2H, s), 3.10 - 3.25 (2H, m), 3.80 - 3.95 (2H, m).Mass (m/z): 231.5 (M+H)4.
86% With ammonia; In methanol; at 20℃; for 12h; To a stirred solution of N-tert butyloxycarbonyl1-oxa-6-aza-spiro[2.5]octane 21 (0.64 g, 3.0 mmols) in methanol(4.0 mL) at r.t., a solution of ammonia (NH3)in methanol (7M, 8.0 mL) was added and the reaction was stirred for 12 hours.The volatiles were removed under reduced pressure to obtain the crude masswhich was triturated with hexanes and ether which yielded the above titledcompound 22c (0.6 g) in 86% yield.1H - NMR CDCl3 (CDCl3): d 3.95 - 3.80 (m, 2H), 3.25 -3.10 (m, 2H), 2.63 (s, 2H), 1.35 - 1.60 (m, 4H), 1.45 (s, 9H). Mass (m/z): 231.5 (M+H)+. Anal. (C11H22N2O3) C, H, N
76% With ammonia; In methanol; at 25 - 40℃; for 40h; tert-Butyl l-Oxa-6-aza-spiro[2.5]octane-6-carboxylate (0.5 grams, 2.34 mmole) was added to methanolic ammonia solution (20 mL, 14.83 % w/v) at room temperature. Then reaction mass was stirred for 40 hours at room temperature in a closed vessel. The progress of the reaction was monitored by TLC. After completion of the reaction (TLC), the reaction mass was concentrated on rotavacuum to obtain the title compound. Yield: 0.41 gram (76%). 'H-NMR(8 ppm): 1.35 - 1.69 (16H, m), 2.61 (2H, s), 3.10 - 3.20 (2H, m), 3.81 -3.90(2H, m); Mass (m/z): 231.3 (M+H)+.
76% With ammonia; In methanol; at 20℃; for 40h; tert-Butyl l-oxa-6-azaspiro[2.5]octane-6-carboxylate (0.5 grams, 2.34 mmole, obtained in the step (i) of preparation 5) was added to methanolic ammonia solution (20 mL, 14.83 % w/v) at RT. Then reaction mass was stirred for 40 hours at RT in a closed vessel. The reaction mass was concentrated under vacuum to obtain the title compound. Weight: 0.41 gram (Yield: 76 %). (0385) - NMR (delta ppm): 1.35 - 1.69 (16H, m), 2.61 - 2.69 (2H, m), 3.10 - 3.20 (2H, m), 3.81 - 3.90 (2H, m); (0386) Mass (m/z): 231.3 (M+H)+ .
69% With ammonia; In methanol; at 20℃; Intermediate 2M: tert-butyl 4-(amiriomethyl)-4-hydroxypiperidine-1 -carboxylate A mixture of intermediate 1A (10.0 g, 46.9 mmol) and ammonia solution (201 mL, 7 M solution in methanol, 1.4 mol) was stirred at r.t. overnight. The solvent was removedunder vacuum and the residue was purified by flash chromatography, silica gel, gradient dichioromethane to methanol:dichloromethane (1:4) to give the title compound (7.4 g, 69% yield) as a white solid. HPLC retention time: 2.15 mm; MS:131 (M+H-100).
69% With ammonia; In methanol; at 20℃; A solution of intermediate 1A (10.0 g, 46.9 mmol) in ammonia (201 ml_, 7 M solution in methanol, 1.4 mol) was stirred at r.t. overnight. The solvent was removed under vacuum and the residue was purified by flash chromatography, silica gel, gradient dichloromethane to methanokdichloromethane (1 :4) to give the title compound (7.4 g, 69% yield) as a white solid. HPLC retention time: 2.15 min; MS: 131 (M+H-100).
69% With ammonia; In methanol; at 20℃; Intermediate 2A: fert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate A mixture of intermediate 1A (10.0 g, 46.9 mmol) and ammonia solution (201 mL, 7 M solution in methanol, 1.4 mol) was stirred at r.t. overnight. The solvent was removed under vacuum and the residue was purified by flash chromatography, silica gel, gradient dichloromethane to methanokdichloromethane (1 :4) to give the title compound (7.4 g, 69% yield) as a white solid. HPLC retention time: 2.15 min; MS: 131 (M+H-100).
60.5% With ammonia; In ethanol; water;Inert atmosphere; A stirred solution of 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (9.0 g, 42.2 mmol) in ethanol (60 ml) was added with ammonia (100 ml). The resulting mixture was stirred under a nitrogen atmosphere overnight. The mixture was concentrated under reduced pressure. The residue was added with water (50 ml) and extracted with ethyl acetate (150 ml*3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane:methanol (20:1) as eluents to give 4-aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (5.87 g, 60.5%) as a white solid. MS m/z (ESI): 231 [M+1]
60.5% With ammonia; In ethanol; A stirred solution of l-oxa-6-aza-spiro [2.5] octane-6-carboxylic acid tert-butyl ester (9.0 g, 42.2 mmol) in ethanol(60 ml) was added with ammonia (100 ml). The resulting mixture was stirred under a nitrogen atmosphere overnight. The mixture was concentrated under reduced pressure. The residue was added with water (50 ml) and extracted with ethyl acetate (150 ml><3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane: methanol (20:1) as eluents to give 4-aminomethyl-4-hydroxy-piperidine-l-carboxylic acid tert-butyl ester (5.87 g, 60.5%) as a white solid. MS m/z (ESI): 231[M+1] ,
With ammonia; In methanol; water; at 0 - 20℃; for 7h; 4-Aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester is prepared from 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (Bourrain et al Bioorg. Med. Chem. Lett. 9(23):3369-3374 (1999)). Concentrated aqueous NH4OH (6 mL) is added to a solution of 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (0.50 g, 2.3 mmol) in MeOH (4 mL) at 0 C. The reaction mixture is removed from the cooling and allowed to warm to room temperature. After 7 hours, the reaction mixture is concentrated under reduced pressure to afford desired product as a white solid.
With ammonium hydroxide; In methanol; at 0 - 20℃; for 16h; aqueous ammonia (6mL)was added to a solution of tert-butyl 1-oxa-6-azaspiro[2.5]octan-6-carboxylate (500mg, 2mmol) in methanol (4mL) at0C. The reaction solution warmed to room temperature and was stirred for 16 hours, then concentrated under reduced pressure to give a colorless oil (530mg, 2.3mmol) with a yield of 100%, which was used directly in the next step withoutpurification.

  • 2
  • [ 392331-66-7 ]
  • C14H16O7 [ No CAS ]
  • [ 819800-94-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; Triethylamine (0.0373 mol, 5.2 ml) then ethyl chloroformate (0.0373 mol) were added dropwise at a temperature between 0C and 5C to a mixture of intermediate (8) (0.0373 mol) in DCM (100 ml) under nitrogen flow. The mixture was stirred at this temperature for 45 minutes (first mixture). Triethylamine (0.0373 mol, 5. 2ml) was added at room temperature to a mixture of intermediate (52) (0.0373 mol) in DCM (100 ml). The mixture was stirred at room temperature for 45 minutes, then added dropwise at a temperature between 0C and 5C to the first mixture. The reaction mixture was stirred at this temperature for 1 hour, then brought to room temperature, stirred for 1 hour and poured out into ice water. DCM was added. The mixture was extracted with DCM. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2CL2/CH30H/NH40H 97/3/0.1). The pure fractions were collected and the solvent was evaporated, yielding 12 g of intermediate (53).
  • 3
  • [ 819800-93-6 ]
  • [ 392331-66-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In methanol; at 14℃; A mixture of intermediate (51) (0.058 mol) and acetic acid (12 ml) in methanol (250 ml) was hydrogenated at 14 C with palladium-on-carbon (10%, 1 G) as a catalyst. After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was taken up into ice/water, then alkalized with potassium hydroxide and salted out with K2CO3. This mixture was extracted twice with DCM. The separated organic layer was dried, filtered and the solvent evaporated. The residue was suspended in DIPE, filtered off, washed and dried, yielding 7.5 g of intermediate (52)
A mixture of intermediate (64) (0.058 mol) and acetic acid (12 ml) in methanol (250 ml) was hydrogenated at 14C with palladium-on-carbon (10%, 1 g) as a catalyst. After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was taken up into ice/water, then alkalized with potassium hydroxide and salted out with K2CO3. This mixture was extracted twice with DCM. The separated organic layer was dried, filtered and the solvent evaporated. The residue was suspended in DIPE, filtered off, washed and dried, yielding 7.5 g of intermediate (65).
With hydrogen;palladium(II) hydroxide/carbon; In ethanol; under 2068.65 Torr; for 120h; A mixture of tert-butyl 4-hydroxy-4-(nitromethyl)piperidine-l -carboxylate (20.42 g, 78.4 mmol) and 20% palladium hydroxide on carbon (1.21 g) in ethanol (250 mL) was hydrogenated at 40 psi (2.8 x 105 Pa) for 3 d on a Parr apparatus. More 20% palladium hydroxide on carbon (1.0 g) was added and the hydrogenation was continued for 2 more days. The mixture was filtered through CELITE filter agent and the filtrate was concentrated to provide tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-l -carboxylate, which was concentrated from toluene (200 mL) to remove residual ethanol before use in the next reaction.
With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 20℃; The mixture of tert-butyl 4-hydroxy-4- (nitromethyl) piperidine-1-carboxylate (15.0 g, 0.058 mol) and acetic acid (12 mL) in methanol (180 mL) was hydrogenated at rt with palladium-on-carbon (10, 1.5 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up into ice water, alkalized with potassium hydroxide, extracted twice with EtOAc, dried over Na2SO4, filtered and concentrated to give tert-butyl 4- (aminomethyl) -4-hydroxypiperidine-1-carboxylate.
With palladium on activated charcoal; hydrogen; acetic acid; In methanol; at 20℃; The mixture of tert- butyl 4-hydroxy-4-(nitromethyl)piperidine-l-carboxylate (15.0 g, 0.058 mol) and acetic acid (12 mL) in methanol (180 mL) was hydrogenated at rt with palladium-on-carbon (10 %, 1.5 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up into ice water, alkalized with potassium hydroxide, extracted twice with EtOAc, dried over Na2S04, filtered and concentrated to give tert-butyl 4-(aminomethyl)-4- hydroxypiperidine- 1 -carboxylate.

  • 4
  • [ 908140-15-8 ]
  • [ 392331-66-7 ]
YieldReaction ConditionsOperation in experiment
59% Step 2. tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate To a suspension of lithium alminium hydride (84 mg, 2.2 mmol) in THF (5 mL), a solution of tert-butyl 4-cyano-4-hydroxypiperidine-1-carboxylate (200 mg, 0.88 mmol, step 1 of Example 22) in THF (1 mL) was added dropwise at 0 C. The mixture was stirred for 1 h at that temperature and Na2SO4.10H2O (400 mg) was added slowly, and the mixture was stirred for 5 h at room temperature. The mixture was filtered though a pad of Celite, washed with CH2Cl2 (20 mL*2), the filtrate was concentrated to give clear colorless oil. The residue was chromatographed on a column of silica gel eluding with CH2Cl2/MeOH/NH4OH (14:1:0.1) to give 120 mg (59%) of the title compound as white solid. 1H-NMR (CDCl3) delta: 3.98-3.75 (2H, m), 3.17 (2H, t, J=10.8 Hz), 2.56 (2H, s), 1.46 (9H, s), 1.60-1.25 (4H, m). Signals due to O and N were not observed.
  • 5
  • acetonitrile-water [ No CAS ]
  • [ 392331-66-7 ]
  • [ 435321-22-5 ]
  • 3-{3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methyl-benzoyl}-1-oxa-3,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; (iii) 3-{3-[2-(2,4-Dichloro-Phenyl)-Ethoxy]-4-Methyl-Benzoyl}-1-Oxa-3,8-Diaza-Spiro[4.5]decane-8-carboxylic acid tert-butyl ester 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methyl-benzoic acid (300 mg, 0.922 mmol) and crude <strong>[392331-66-7]4-aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester</strong> (212.5 mg, 0.922 mmol) was dissolved in 5 ml DMF. After cooling to -15 C. HATU (386 mg, 1 mmol) and N-ethylmorpholine (318.9 mg, 2.77 mmol) were added. The mixture was stirred at 0 C. for 2 hours and at room temperature for 15 hours, evaporated and purified on RP18 (5mum) (gradient acetonitrile water 90:10 to 0:100). The fractions containing the product were evaporated and lyophilised. The product was obtained as its trifluoroacetate salt.
  • 6
  • 4-Cyano-4-trimethylsilanyloxy-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 392331-66-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In tetrahydrofuran; (ii) 4-Aminomethyl-4-Hydroxy-Piperidine-1-Carboxylic Acid Tert-Butyl Ester 4-Cyano-4-trimethylsilanyloxy-piperidine-1-carboxylic acid tert-butyl ester (7.5 g) was dissolved in 100 ml of tetrahydro-furan under an argon atmosphere. A solution of lithium aluminium hydride in tetrahydro-furan (30 ml, 1 molar) was dropwise added at 0 C. After stirring for 15 hours at room temperature, a sodium hydroxide solution (20%) was slowly added under cooling. The solid was filtered after dilution with ethyl acetate and the organic layer evaporated. The crude material contains a mixture of the desired product (MS: 231.2 (M+H)+) and the corresponding trimethylsiliyl ether (MS: 303.1 (M+H)+) and was used without further purification.
  • 7
  • [ 392331-66-7 ]
  • [ 85967-19-7 ]
  • [ 879514-94-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; Under a nitrogen atmosphere a solution of tert-butyl 4-(aminomethyl)-4- hydroxypiperidine-1 -carboxylate (38.9 g, 169 mmol, prepared according to Parts A and B of Example 4) in dichloromethane (420 mL) was cooled to 0 0C. Triethylamine (23.6 mL, 169 mmol) was added followed by the portionwise addition of 4-chloro-3- nitronaphthyridine (30.8 g, 147 mmol). The reaction mixture was stirred at ambient temperature overnight and then diluted with saturated aqueous sodium bicarbonate (200 mL). The layers were separated and the aqueous was extracted with dichloromethane (3 x 100 mL). The combined organics were concentrated under reduced pressure to provide a dark yellow solid. This material was triturated with saturated aqueous sodium bicarbonate, isolated by filtration, rinsed well with water, and then dried in a vacuum oven at 70 C overnight to provide 58.85 g of tert-butyl 4-hydroxy-4-[(3- nitro[l,5]naphthyridin-4-yl)amino]methyl}piperidine-l-carboxylate as a yellow solid.
  • 8
  • [ 392331-66-7 ]
  • [ 39061-97-7 ]
  • [ 879514-18-8 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In dichloromethane; for 2h;Heating / reflux; To a solution of tert-butyl 4-(aminomethyl)-4-hydroxypiperidme-l -carboxylate (78.4 mmol, prepared as described above) in dichloromethane (300 mL) was added triethylamine (11 mL, 79 mmol) and 4-chloro-3-nitroquinoline (12.7 g, 61.2 mmol). The mixture was stirred at rt for 1 h, then heated at reflux for 1 h. The solution was transferred to a separatory funnel and extracted with water (100 mL). The organic layer was isolated and upon standing a precipitate formed. The solid was isolated by filtration and washed with dichloromethane and water and dried. Additional solid precipitated from the mother liquor and was isolated. The two yellow solids were combined and dried to yield tert- butyl 4-hydroxy-4-[(3-nitroqumolin-4-yl)amino]methyl}piperidine4 ^ (20.23 g, 82%).
  • 9
  • [ 392331-66-7 ]
  • [ 26228-68-2 ]
YieldReaction ConditionsOperation in experiment
74% A stirred mixture of <strong>[392331-66-7]4-aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester</strong> (529 mg, 2.3 mmol) in tetrahydrofuran (15 ml) was added slowly with lithium aluminum hydride (0.88 g, 23 mmol) while maintaining the temperature at 0~5 C. Upon completion of the addition, the mixture was stirred at 80 C. in oil bath overnight. The mixture was added with potassium sodium tartrate tetrahydrate (6.3 g, 22.3 mmol) and stirred for 8 hours at room temperature. The mixture was filtered and washed with tetrahydrofuran (10 ml*3). The combined organic extracts were concentrated under reduced pressure to give 4-aminomethyl-1-methyl-piperidin-4-ol (245 mg, 74%) as a white oil which was used as such. MS m/z (ESI): 145 [M+1]
74% A stirred mixture of 4-aminomethyl-4-hydroxy-piperidine-l-carboxylic acid tert-butyl ester (529 mg, 2.3 mmol) in tetrahydrofuran (15 ml) was added slowly with lithium aluminum hydride (0.88 g, 23 mmol) while maintaining the temperature at 0-~5C. Upon completion of the addition, the mixture was stirred at 80 C in oil bath overnight. The mixture was added with potassium sodium tartrate tetrahydrate (6.3 g, 22.3 mmol) and stirred for 8 hours at room temperature. The mixture was filtered and washed with tetrahydrofuran (10 mlx3). The combined organic extracts were <n="157"/>concentrated under reduced pressure to give 4-aminomethyl-l-methyl-piperidin-4-ol (245 mg, 74%) as a white oil which was used as such. MS m/z (ESI): 145[M+1]A solution of 2-carboxvmethyl
  • 10
  • [ 392331-66-7 ]
  • [ 79-04-9 ]
  • [ 1160247-07-3 ]
  • 11
  • [ 392331-66-7 ]
  • [ 1361955-58-9 ]
  • tert-butyl 4-hydroxy-4-((2-methoxy-6-pentadecylbenzylamino)methyl)piperidine-1-carboxylate [ No CAS ]
  • 12
  • [ 392331-66-7 ]
  • [ 667-27-6 ]
  • [ 1179337-13-3 ]
YieldReaction ConditionsOperation in experiment
99% In N,N-dimethyl-formamide; for 1h;Inert atmosphere; [00350] Preparation of 4-(but-2-ynyl)-2,2-difluoro-l-oxa-4,9- diazaspiro[5.5]undecane[00351] Step 1:To a solution of tert-butyl 4-(aminomethyl)-4-hydroxy-piperidine-l-carboxylate (3.00 g, 13.0 mmol) in N,N-dimethylformamide (30 mL) was added ethyl 2-bromo-2,2- difluoro-acetate (2.65 g, 13.0 mmol) and the reaction mixture stirred for 1 h under nitrogen. The reaction mixture was mixture diluted with ethyl acetate and water (25 mL) and brine (25 mL). The organic layer was dried over Na2S04, filtered and concentrated to provide tert-butyl 4-[[(2-bromo-2,2-difluoro-acetyl)amino]methyl]-4- hydroxy-piperidine- l-carboxylate (4.98 g, 12.9 mmol, 99%). NMR (400 MHz, OMSO-d6) delta 9.04 (t, J = 5.9 Hz, 1H), 4.66 (s, 1H), 3.65 (d, J = 12.7 Hz, 2H), 3.16 (d, J = 6.1 Hz, 2H), 3.02 (s, 2H), 1.38 (m, 13H).
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Aliphatic Heterocycles

Chemical Structure| 169206-55-7

[ 169206-55-7 ]

tert-Butyl 2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate

Similarity: 0.94

Chemical Structure| 181269-70-5

[ 181269-70-5 ]

tert-Butyl 4-hydroxy-3-methylpiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 406235-30-1

[ 406235-30-1 ]

1-Boc-4-Hydroxy-4-methylpiperidine

Similarity: 0.94

Chemical Structure| 1179338-62-5

[ 1179338-62-5 ]

tert-Butyl 4-(2-aminoethyl)-4-hydroxypiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 301221-57-8

[ 301221-57-8 ]

tert-Butyl 4-(2-amino-1-hydroxyethyl)piperidine-1-carboxylate

Similarity: 0.92

Piperidines

Chemical Structure| 169206-55-7

[ 169206-55-7 ]

tert-Butyl 2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate

Similarity: 0.94

Chemical Structure| 181269-70-5

[ 181269-70-5 ]

tert-Butyl 4-hydroxy-3-methylpiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 406235-30-1

[ 406235-30-1 ]

1-Boc-4-Hydroxy-4-methylpiperidine

Similarity: 0.94

Chemical Structure| 1179338-62-5

[ 1179338-62-5 ]

tert-Butyl 4-(2-aminoethyl)-4-hydroxypiperidine-1-carboxylate

Similarity: 0.94

Chemical Structure| 301221-57-8

[ 301221-57-8 ]

tert-Butyl 4-(2-amino-1-hydroxyethyl)piperidine-1-carboxylate

Similarity: 0.92

; ;