HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (S)-2-cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Benzyloxycarbonyl-L-proline | HCID 101987 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-2-cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester | HCID 69997288 | 85.6% |
Reaction Steps
A mixture of carbobenzyloxy-L-proline (994 mg, 3.99 mmol), cyclopropylamine (0.41 mL, 5.9 mmol), HOBt (807 mg, 6 mmol), EDC (1.12 g, 5.9 mmol) and TEA (1.1 mL) in DMF (11 mL) was stirred at room temperature for 48 hours. The reaction was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was column chromatographed to give 985 mg (81%) of (S)-2-cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06599902B2 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-ff4ae6a4a34f441d9182894a06fff6d9 |
| Source note | uspto-grants-2003_07 |