Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate → {(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

HRID 1468760노트

반응식

HRID 1468760 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[N:12]([C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:11][C@@H:10]([C:21](OC)=[O:22])[CH2:9]1>COC1CCCC1>[C:15]1([C@H:13]([N:12]2[CH2:8][CH2:9][C@H:10]([CH2:21][OH:22])[CH2:11]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

4

반응물 2

HCID 13772852Methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 13772859{(3S)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol수율 57%

시약·촉매·용매 1

HCID 138539Cyclopentyl methyl ether용매

실험 절차

To a slurry of lithium aluminum hydride (4.55 g, 120 mmol) in cyclopentyl methyl ether (100 ml) at 0° C. under nitrogen atmosphere was added methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (14.0 g, 56.5 mmol) dropwise. The resulting mixture was stirred for 15 minutes and gradually warmed to room temperature. After one hour, the reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C. and the resulting solid materials were removed by filtration. Concentration of the filtrate afforded {(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}methanol (6.62 g, 32 mmol, 57%). This compound was used for the next reaction without further purification.

후처리

  1. waitAfter one hour
  2. customthe reaction was quenched by the addition saturated sodium sulfate aqueous solution at 0° C.
  3. customthe resulting solid materials were removed by filtration

출처 및 근거

ORD 기록
ord-d2c9d289db4b41f8a3d6af93a58ee3f2
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006232B2

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