Benzyl chloroformate → HCID 21971261, compound

HRID 1954606Notes

Reaction equation

HRID 1954606 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:10]2([F:23])[F:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl>[CH2:28]([O:27][C:25]([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:10]([F:22])([F:23])[CH2:11]1)=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 21971267HCID 21971267, compound

Product 1

HCID 21971261HCID 21971261, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(R)-(1-Ethoxycarbonylcyclopropyl)-3,3-difluoro-1-[1-(S)-phenylethyl]pyrrolidine(2.536 g, 7.842 mmol) was dissolved in dry dichloromethane (80 ml), and benzyl chloroformate (2.80 ml, 19.6 mmol) was added dropwise to the thus prepared solution which was cooled in an ice bath. The reaction solution was stirred at room temperature for 44 hours and then 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=4:1, to thereby obtain 2.294 g (82.8%) of the title compound as a colorless oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. customdichloromethane was evaporated under reduced pressure
  3. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-b093a4cad17d436982512cd161864b9d
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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