HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl 2-(4-bromo-3-fluorophenyl)pyrrolidine-1-carboxylate | HCID 66620873 | — |
| Reactant | HCID 178418416 | HCID 178418416 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate | HCID 66621283 | 120.1% |
Reaction Steps
A mixture of benzyl 2-(4-bromo-3-fluorophenyl)pyrrolidine-1-carboxylate (15.3 g, 40.6 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride (1.67 g, 2.0 mmol) and triethylamine (8.4 mL, 60.9 mmol) in methanol (180 mL) was stirred under 60 psi of carbon monoxide at 100° C. for 4 hour. After cooling to ambient temperature, the mixture was concentrated and the residue purified by flash chromatograph on silica gel using a gradient of 8-15% ethyl acetate in petroleum ether to give benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate as colorless oil (8.71 g, yield 60%). LC-MS (ESI) m/z: 358 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088760B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-c220e25a994d417eabcd62dcbabc6b30 |
| Source note | uspto-grants-2012_01 |