HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1,1-Dimethylethyl (3R)-3-[(cyclopropylcarbonyl)amino]-1-pyrrolidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropanecarboxylic acid | HCID 15655 | — |
| Reactant | (R)-(+)-1-Boc-3-aminopyrrolidine | HCID 854070 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1,1-Dimethylethyl (3R)-3-[(cyclopropylcarbonyl)amino]-1-pyrrolidinecarboxylate | HCID 58683897 | 73.4% |
Reaction Steps
To a mixture of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (500 mg, 2.68 mmol) in CH2Cl2 (101 mL) was added cyclopropanecarboxylic acid (276 μL, 3.48 mmol), followed by the addition of HATU (1.3 g, 3.48 mmol) and triethylamine (725 μL, 5.2 mmol). The reaction was complete after stirring for 1 h. After quenching with water, the aqueous layer was extracted twice with CH2Cl2, and the combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude material was purified via silica gel chromatography 0-20% EtOAc/CH2Cl2 to afford (R)-tert-butyl 3-(cyclopropanecarboxamido)pyrrolidine-1-carboxylate (500 mg, 73%). LC/MS: m/z 255.3 (M+H)+ at 2.33 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07928107B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-7822bf64be424a28ba88f06129208dbe |
| Source note | uspto-grants-2011_04 |