3,3-Diphenylpyrrolidine → HCID 45274933, compound

Participants

Reaction Steps

To a solution of 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid (Example 90D, 0.345 g, 1.0 mmol) in dichloromethane (20 mL) under nitrogen was added 3,3-diphenylpyrrolidine (Example 17A, 0.223 g, 1.0 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.383 g, 2.0 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 200 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (Analogix®, Burlington, Wis.) eluting with ethyl acetate/hexane (1:1) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.32-7.15 (m, 14H), 6.98 (t, J=8.7, 4H), 4.22 (d, J=3.0, 2H), 4.09 (d, J=3.5, 2H), 3.62-3.45 (m, 4H), 2.67-2.49 (m, 4H), 1.84 (d, J=5.6, 2H); MS (DCI) m/z 551.2 (M+H)+.

Provenance & Evidence