1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[cyclopropyl(phenyl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

Participants

Reaction Steps

A solution of cyclopropyl(phenyl)methanamine hydrogen chloride (0.050 g, 0.272 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.073 g, 0.247 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.066 mL, 0.371 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 7.20-7.39 (m, 13H), 7.14-7.18 (m, 2H), 6.44 (d, J=8.1 Hz, 1H), 4.32 (t, J=8.6 Hz, 1H), 4.05 (d, J=15.3 Hz, 1H), 4.03 (d, J=15.6 Hz, 1H), 3.42-3.56 (m, 2H), 2.73-2.88 (m, 2H), 0.81-0.97 (m, 1H), 0.39-0.56 (m, 2H), 0.21-0.37 (m, 2H); MS (ESI−) m/z 423 (M−H)−.

Provenance & Evidence