HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid | HCID 688022 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 69832143 | 63% |
Reaction Steps
(2R)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.15 g, 10 mmol) reacted with morpholine (1.3 mL, 15 mmol) in CH2Cl2 (30 mL) in the presence EDC (2.7 g, 15 mmol), HOBT (1.9 g, 15 mmol) and Et3N (2.1 mL, 15 mmol) at r.t. for 14 h. The mixture was evaporated to dryness and purified by column chromatography. After washing the resulting solid with aqueous NaHCO3 followed by H2O to remove HOBT contamination, pure compound (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 11a (1.79 g, 63%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06642232B2 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-cb98b0ab204440b8b8bbdb6d68f3c7fd |
| Source note | uspto-grants-2003_11 |