HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride | HCID 68614460 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl ester | HCID 10428462 | 76.5% |
Reaction Steps
A solution of 250 mg (0.74 mmol) of (RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride [Example 1f)] in 12 ml of dichloromethane is cooled to 0° C. and successively treated with 226 μl (1.6 mmol) of triethylamine and 64 μl (0.8 mmol) of methyl chloroformate. The mixture is left to warm to RT and stirred for 1 hour. For the working-up, dichloromethane and water are added to the reaction mixture. The organic layer is separated, dried over sodium sulfate, and evaporated. There are obtained 203 mg (76% of theory) of (RS)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamic acid methyl ester as a white solid. MS: m/e=359 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07151111B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-68e38b5ce4c8483bb4f257f2c42c5b93 |
| Source note | uspto-grants-2006_12 |