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

HRID 635090Notes

Reaction equation

HRID 635090 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-991aa0d7e6cb4bb4b3c662294e96034a
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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