1-Phenylcyclobutylamine → 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-(1-phenylcyclobutyl)acetamide

Participants

Reaction Steps

A solution of 1-phenylcyclobutanamine (0.030 g, 0.204 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.055 g, 0.185 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.036 g, 0.185 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 7.31-7.39 (m, 7H), 7.17-7.31 (m, 8H), 6.42-6.44 (br s, 1H), 3.94 (s, 2H), 3.46 (t, J=6.5 Hz, 2H), 2.79 (t, J=6.5 Hz, 2H), 2.42-2.52 (m, 2H), 2.19-2.30 (m, 2H), 1.71-1.95 (m, 2H); MS (ESI−) m/z 423 (M−H)−.

Provenance & Evidence