(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine → (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

HRID 743298ノート

反応式

HRID 743298 の反応式
C([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([OH:8])[CH2:10][CH:11]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

参加物

5

反応物 2

HCID 53917409(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 54118331(4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine収率 97.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 390 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in step (a) above] in 25 ml of ethanol was stirred at 60° C. for 5 hours in an atmosphere of hydrogen at atmospheric pressure and in the presence of 100 mg of 5% w/w palladium-on-charcoal. At the end of this time, the catalyst was removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 310 mg (yield 97%) of the title compound as a colorless oil.

後処理

  1. customAt the end of this time, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-96b0b7b16c624b7faf46fd1cc975fc94
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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