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
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | rel-(3aR,6aR)-Methyl 2-benzylhexahydrocyclopenta[c]pyrrole-3a(1H)-carboxylate | HCID 1515514 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1R*,5R*)-3-Benzyloxycarbonyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester | HCID 67490894 | 45% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08618094B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-85ac0279b792423298a5545fc769e049 |
|---|
| Source note | uspto-grants-2013_12 |
|---|