441716-79-6|(2S,5S)-tert-Butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate| Ambeed

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CAS No. :	441716-79-6
Formula :	C₁₁H₂₁NO₃
M.W :	215.29
SMILES Code :	O=C(N1[C@H](CO)CC[C@@H]1C)OC(C)(C)C
MDL No. :	MFCD28119177

Yield	Reaction Conditions	Operation in experiment
94.3%	With borane; In tetrahydrofuran; at 0 - 25℃; for 2h;	[001661 To a cooled 0 °C solution of compound 1-6 (2.24 g, 9.78 mmol) in THF (20 mL) was added a solution of borane in THF (14.6 mL, 1 mol/L). The mixture was stirred at 25 °C for 2 hours, and then to the mixture was added MeOH (8.0 mL). The THF was removed /n vacuo and the residue was dissolved in DCM (30 mL). The resulting mixture was washed with water (20 mLx3). The separated organic phase was dried over anhydrous Na2504 and concentrated /n vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as colorless oil (1.98 g, 94.3percent). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) m/z: 216.2 [M+Hfb; and?H NMR (400 MHz, CDC13): 3.90-3.91 (br, 2H), 3.62-3.65 (m, 2H), 3.50-3.54 (m, 1H), 1.91-1.93 (m, 2H), 1.51-1.60 (m, 2H), 1.44 (s, 9H), 1.13-1.14 (d,J= 6.2 Hz, 3H) ppm.
93%		To a solution of <strong>[334769-80-1](2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid</strong> (5.91 g, 25.8 mmol) in tetrahydrofuran at 0° C., was added borane in dimethylsulfide (1.0 M, 3.4 mL, 34 mmol) dropwise. The reaction was stirred for 4 hours at 0° C. then 18 hours at room temperature. The mixture was then cooled to 0° C. and methanol (70 mL) was added dropwise. The reaction was warmed to room temperature and the solvents were removed in vacuo. The residue was taken up in dichloromethane (200 mL) and extracted with saturated sodium bicarbonate. The organic layer was dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate as a clear oil (5.15 g, 23.9 mmol, 93percent) and was used directly in the following step.
		Example 17, Step hTo a solution of (2S,5S)-l-(tert-butoxycarbonyl)-5-methylpyrrolidine-2- carboxylic acid (3.5 g, 15.27 mmol) in THF (10 mL) was added BH3.DMS (1.595 mL, 16.79 mmol) at 0 °C and then refluxed at 80 °C for 12 h. The reaction mixture was cooled to 0 °C and added slowly MeOH (10 mL). After stirring for 10 minutes the volatile components were removed under reduced pressure. The resulting residue was dissolved in EtOAc (50 mL), washed with 10percent NaHC03 (25 mL), water (25 mL), brine (10 mL), dried over Na2S04 and concentrated in vacuum. The crude was purified by flash chromatography (Silica gel 230-400, 30-40percent EtO Ac/petroleum ether) to obtain 17h (3.1 g) as a colorless liquid. LC/MS (Condition 75): Rt = 1.71 min. XH NMR (CDC13> delta = 7.26 ppm, 400 MHz): delta 4.95 (br s, 1H), 3.98-3.88 (m, 2H), 3.71-3.63 (m, 1H), 3.57-3.50 (m, 1H), 2.03-1.89 (m, 2H), 1.72-1.50 (m, 2H), 1.47 (s, 9H), 1.16 (d, J = 6.0, 3H). LC/MS: Anal. Calcd. for [M+H-Boc]+ C6H14NO: 116.10; found 116.2.

	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 22h;	(2S,5S)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-l-carboxylate To a solution of (2S,5S)-l -(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid (5.91 g, 25.8 mmol) in tetrahydrofuran at 0 °C, was added borane in dimethylsulfide (1.0 M, 3.4 mL, 34 mmol) dropwise. The reaction was stirred for 4 hours at 0 °C then 18 hours at room temperature. The mixture was then cooled to 0 °C and methanol (70 mL) was added dropwise. The reaction was warmed to room temperature and the solvents were removed in vacuo. The residue was taken up in dichloromethane (200 mL) and extracted with saturated sodium bicarbonate. The organic layer was dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-tert-butyl 2- (hydroxymethyl)-5-methylpyrrolidine-l -carboxylate as a clear oil (5.15 g, 23.9 mmol, 93percent) and was used directly in the following step.
	With borane-THF; In tetrahydrofuran; at 0 - 25℃; for 2h;	Step 6) the Preparation of Compound 1-7 (0234) To a cooled 0° C. solution of compound 1-6 (2.24 g, 9.78 mmol) in THF (20 mL) was added a solution of borane in THF (14.6 mL, 1 mol/L). The mixture was stirred at 25° C. for 2 hours, and then to the mixture was added MeOH (8.0 mL). The THF was removed in vacuo and the residue was dissolved in DCM (30 mL). The resulting mixture was washed with water (20 mL×3). The separated organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=3/1) to give the title compound as colorless oil (1.98 g, 94.3percent). The compound was characterized by the following spectroscopic data: (0235) MS (ESI, pos. ion) m/z: 216.2 [M+H]+; and (0236) 1H NMR (400 MHz, CDCl3): delta 3.90-3.91 (br, 2H), 3.62-3.65 (m, 2H), 3.50-3.54 (m, 1H), 1.91-1.93 (m, 2H), 1.51-1.60 (m, 2H), 1.44 (s, 9H), 1.13-1.14 (d, J=6.2 Hz, 3H) ppm

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CAS No.: 441716-79-6

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CAS No.: 441716-79-6

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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
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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
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