Benzyl chloroformate → HCID 68862532, compound

HRID 229544Notes

Reaction equation

HRID 229544 reaction equation
[F:1][CH:2]1[CH2:6][N:5]([C@@H](C2C=CC=CC=2)C)[CH2:4][C@@:3]1([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:23]([O:30][C:31]([N:5]1[CH2:6][CH:2]([F:1])[C@:3]([CH3:22])([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 57758696HCID 57758696, compound

Product 1

HCID 68862532HCID 68862532, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl(3S)-4-fluoro-3-methyl-1-[(1R)-1-phenylethyl]-pyrrolidine-3-carboxylate (isomer A) (2.15 g, 6.99 mmol) in dichloromethane (40 mL), benzyloxycarbonyl chloride (1.50 mL, 10.5 mmol) was added, and the mixture was stirred in an oil bath at 60° C. for 20 hours. After concentrating the reaction mixture under reduced pressure, the concentrate was purified by silica gel column chromatography (elusion by hexane:ethyl acetate, 12:1→2:1) to obtain 1.81 g (77%) of the title compound (isomer A) as a colorless oily substance.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure
  2. customthe concentrate was purified by silica gel column chromatography (elusion by hexane:ethyl acetate, 12:1→2:1)

Sources & evidence

ORD record
ord-586c674fa7c5448daf3ccf9dbe61c420
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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