HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Iodide → (R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Fluoro-2-nitrobenzotrifluoride | HCID 223094 | — |
| Reactant | (R)-(+)-1-Boc-3-aminopyrrolidine | HCID 854070 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 58576068 | 99.3% |
Reaction Steps
(R)-3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (559 mg; 3.0 mmol), 4-fluoro-1-nitro-2-trifluoromethyl-benzene (627 mg; 3.0 mmol), potassium carbonate (1.24 g; 9.0 mmol), potassium iodide (498 mg; 3.0 mmol), acetonitrile (6 mL) and water (2 mL) are mixed together and the resulting reaction mixture heated to efflux for 5 hours. The phases are separated and the organic phase dried (MgSO4) and concentrated under high vacuum. The residue is then triturated with diethyl ether, dried under high vacuum to afford the desired compound (1.12 g; 2.98 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096524B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-f08bba484fb3443ead0969f4ddd6f62b |
| Source note | uspto-grants-2015_08 |