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

HRID 1468760ノート

反応式

HRID 1468760 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 138539Cyclopentyl methyl ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2c9d289db4b41f8a3d6af93a58ee3f2
出典データセット
uspto-grants-2015_04
特許番号
US09006232B2

反応ノート

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