HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 4-Nitrobenzoyl chloride | HCID 8502 | — |
| Reactant | 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 23571603 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 66870738 | 72% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
Compound 21a (11.8 g, 32.0 mmol) and pyridine (27 ml, 305 mmol) were dissolved in DCM (200 ml) and cooled to 0° C., 4-nitrobenzoyl chloride (6.6 g, 35.6 mmol) was added and the solution was stirred at room temperature overnight. The reaction mixture was washed with NaHCO3 (aq), aqueous citric acid and brine, dried over MgSO4 and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane: 50:50) to give 11.84 g, 72% of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08383584B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-ecf25c2bbdc3430f96210f97feaea924 |
| Source note | uspto-grants-2013_02 |