Ethyl Acetate → 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidine

Participants

Reaction Steps

Trifluoroacetic acid (9 μL, 128 μmol) was added to (1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide (1.00 g, 93% purity, 2.56 mmol) in toluene (1.28 mL). N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (911 mg, 3.84 mmol) in toluene (8.75 mL) was added at room temperature over one hour. The solvents of the reaction mixture were removed and the crude product was taken up in iso-propanol and the pH was adjusted to 3 with 3.6% hydrochloric acid. After two hours the formed crystals were filtered off. 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoro-methyl)pyrrolidinium chloride (1.17 g, 95% purity, 86% yield) was obtained. The hydrochloride was suspended in aqueous sodium hydroxide (2 N, 5 mL) and ethyl acetate was added. The mixture was stirred until two clear phases were formed. The organic phase was separated, dried over sodium sulfate, filtered and evaporated. This procedure yielded 1-benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidine (1.07 g, 95% purity, 80% yield).

Provenance & Evidence