1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[2-(5-fluoro-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-3,3-diphenylpyrrolidin-2-one

Participants

Reaction Steps

A solution of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.067 mL, 0.381 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.075 g, 0.254 mmol) and 5-fluoroisoindoline hydrochloride (0.044 g, 0.254 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 7.13-7.40 (m, 11H), 6.88-7.05 (m, 2H), 4.75-4.81 (m, 4H), 4.23 (s, 2H), 3.60 (t, J=6.6 Hz, 2H), 2.85 (t, J=6.6 Hz, 2H); MS (ESI+) m/z 415 (M+H)+.

Provenance & Evidence