Benzyl chloroformate → 1-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine

HRID 1954612ノート

反応式

HRID 1954612 の反応式
[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H](C3C=CC=CC=3)C)[CH2:11][C@H:10]2[F:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>ClCCl>[CH2:27]([O:26][C:24]([N:12]1[CH2:13][C@H:9]([C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:7]2)[C@H:10]([F:22])[CH2:11]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

4

反応物 2

HCID 10387Benzyl chloroformateHCID 109687574-(S)-(1Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]pyrrolidine

生成物 1

HCID 110350361-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine収率 83.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]pyrrolidine (5.08 g, 16.63 mmol) was dissolved in dry dichloromethane (50 ml), and benzyl chloroformate (3.56 ml, 25.0 mmol) was added dropwise to the thus prepared solution which was cooled in an ice bath. After 1 hour of heating of the reaction solution under reflux, dichloromethane was evaporated under reduced pressure. Thereafter, the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=3:1, to thereby obtain 4.67 g (83.7%) of the title compound as a colorless oil.

後処理

  1. temperaturewas cooled in an ice bath
  2. temperatureAfter 1 hour of heating of the reaction solution
  3. temperatureunder reflux
  4. customdichloromethane was evaporated under reduced pressure
  5. washeluted with an eluant of n-hexane

出典と根拠

ORDレコード
ord-e519129ab33645ce8c8cbe146ae3b676
出典データセット
uspto-grants-2000_09
特許番号
US06121285

反応ノート

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