Benzyl chloroformate → HCID 69847508, compound

HRID 1356556Notes

Reaction equation

HRID 1356556 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:26][C@H:25]2[C@H:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)C1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([N:19]1[CH2:26][C@H:25]2[C@H:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 13463770cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Product 1

HCID 69847508HCID 69847508, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyloxycarbonyl chloride (4.28 ml, 30.0 mmol) in dichloromethane (15 ml) was added dropwise to a solution of (1R,5S)-7-benzyl-2-oxo-7-azabicyclo[3.3.0]octane (1.31 g, 6.10 mmol) in dichloromethane (20 ml) while cooling with ice, and the mixture was stirred at room temperature for 16 hours. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 1.36 g (5.24 mmol, 86%) of the title compound as a colorless oily substance.

Workup

  1. temperaturewhile cooling with ice
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-615ac4a8b9b742d3a73b542d9b8cb711
Source dataset
uspto-grants-2003_07
Patent number
US06586604B2

Reaction notes

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