4-Methylmorpholine → 2-[3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

Participants

Reaction Steps

To a suspension of 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.200 g, 0.604 mmol; Example 58D) in dichloromethane (2 mL) was added a catalytic amount of N,N-dimethylformamide followed by oxalyl dichloride (2.0 Min dichloromethane) (0.453 mL, 0.905 mmol). After stirring for 30 minutes, the reaction was concentrated. The residue was dissolved in dichloromethane (2 mL) and 4-(trifluoromethyl)aniline (0.056 mL, 0.453 mmol) followed by 4-methylmorpholine (0.100 mL, 0.905 mmol) were added. After stirring for 1 hour, the reaction was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 65% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 7.51 (d, J=8.6, 2H), 7.40 (d, J=8.5, 2H), 7.34-7.27 (m, 4H), 7.06-6.96 (m, 4H), 4.16 (s, 2H), 3.60 (t, J=6.5, 2H), 2.82 (t, J=6.5, 2H); MS (ESI+) m/z 474.8 (M+H)+.

Provenance & Evidence