HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 3,5-Bis(trifluoromethyl)benzylamine | HCID 521099 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester | HCID 67548133 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester | HCID 86625300 | 63% |
Reaction Steps
Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (100 mg, 0.428 mmol) and 3,5-bis-trifluoromethyl-benzylamine (125 mg, 0.514 mmol) were dissolved in dry DCM (2 mL), acetic acid (0.1 mL) and NaBH(OAc)3 (180.6 mg, 0.856 mmol) was then added. After stirred for 3 hours the reaction mixture was diluted with DCM, washed with saturated NaHCO3 (cautiously), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography to afford the title product 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester 124 mg (63%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528136B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-c07eb75d69254aa99897fdb1cf0a859d |
| Source note | uspto-grants-2009_05 |