2,2-Diphenylpropylamine → 2-[3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]-N-(2,2-diphenylpropyl)acetamide

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Reaction Steps

To a solution of 2,2-diphenylpropan-1-amine (0.21 g, 1.00 mmol) in dichloromethane (25 mL) under nitrogen was added 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (Example 58D, 0.33 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.39 g, 2.00 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). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.10-7.29 (m, 14H), 6.94-7.01 (m, 4H), 5.66 (t, J=5.4 Hz, 1H), 3.95 (d, J=5.8 Hz, 2H), 3.89 (s, 2H), 3.27 (t, J=6.4 Hz, 2H), 2.55 (t, J=6.4 Hz, 2H), 1.59 (s, 3H); MS (DCI+) m/z 525 (M+H)+.

Provenance & Evidence