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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1917331Generated: October 26, 2026

Benzyl chloroformate → (1R*,5R*)-3-Benzyloxycarbonyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester

https://huagongshe.com/reaction/1917331

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzyl chloroformateHCID 10387—
Reactantrel-(3aR,6aR)-Methyl 2-benzylhexahydrocyclopenta[c]pyrrole-3a(1H)-carboxylateHCID 1515514—
SolventDichloromethaneHCID 6344—
Product(1R*,5R*)-3-Benzyloxycarbonyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl esterHCID 6749089445%

Reaction Conditions

Temperature40 °C

Reaction Steps

Benzyl chloroformate (3.53 mL, 24.6 mmol) was added to a solution of (1R*,5R*)-3-benzyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester (4.27 g, 16.46 mmol) in dichloromethane (50 mL) at room temperature, and the mixture was stirred on an oil bath at 40° C. for 23 hours. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20→67:33) to give 2.24 g (45%) of the title compound as a colorless transparent oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618094B2
Source datasetuspto-grants-2013_12
ORD IDord-85ac0279b792423298a5545fc769e049
Source noteuspto-grants-2013_12