4-Fluorobenzylamine → N-(4-fluorobenzyl)-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

Participants

Reaction Steps

A solution of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.050 g, 0.169 mmol) and (4-fluorophenyl)methanamine (0.023 g, 0.186 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.20-7.30 (m, 9H), 7.06-7.12 (m, 2H), 6.93-6.99 (m, 2H), 6.24-6.27 (m, 1H), 4.26 (d, J=5.9 Hz, 2H), 4.04 (s, 3H), 3.49 (t, J=6.5 Hz, 2H), 2.80 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 401 (M−H)−.

Provenance & Evidence