Sodium Hydroxide → 1-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

Magnesium (47.3 mg, 1.94 mmol), lithium chloride (41.2 mg, 972 μmol) and 1-benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfonyl)-3-(trifluoromethyl)pyrrolidine (500 mg, 972 μmol) were put in a flask under argon atmosphere. Methanol (5 mL) was added and the reaction was stirred for 4.5 hours and one additional hour after adding more magnesium (2 eq.). After standing over night the reaction was heated to 45° C. for seven hours adding magnesium (1 eq. each) after two and five hours. Again after standing over night magnesium was added (1 eq.) and the reaction heated to 45° C. for three hours. Water (2 mL) and methanol was added. After cooling to room temperature sodium hydroxide solution (10%) was added. The precipitate was filtered off, dissolved in ethyl acetate and methanol, washed with hydrochloric acid (10%). The organic phase was dried over sodium sulfate, filtered and the solvents evaporated. The crude 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (308 mg, 69% purity, 59% yield) was crystallized from iso-propanol (111 mg, 95% purity, 29% yield).

Provenance & Evidence