Benzyl chloroformate → HCID 69847508, compound

HRID 1934488Notes

Reaction equation

HRID 1934488 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-7c36caa82233468ea9b49b836dfc8e05
Source dataset
uspto-grants-2002_05
Patent number
US06384050B1

Reaction notes

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