Formic Acid → 1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Participants

Reaction Steps

1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,3-dihydro-1H-pyrrole (200 mg, 82% purity, 440 μmol) was dissolved in methanol (5 mL) under an argon atmosphere. Formic acid (200 μL, 5.30 mmol) and platinum on charcoal (5 w/w % Pt/C, ˜60% H2O, 42.9 mg, 4.4 μmol) was added and the flask was charged with hydrogen (balloon). The reaction was stirred for six hours at room temperature and then left standing over night. After the addition of platinum on charcoal (0.5 mol %) and formic acid (1 mL) the reaction mixture was warmed to 40-50° C. for six hours and then left standing at room temperature. Refluxing the mixture for three more hours and addition of more platinum on charcoal (1.0 mol %) after one hour led to complete conversion. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), filtered over celite, washed with saturated sodium bicarbonate and brine solution. The organic phase was dried over sodium sulfate, filtered and the solvents evaporated. 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine was obtained (163 mg, 97% purity, 96% yield).

Provenance & Evidence