Diisopropylethylamine → 1-{2-[4-(4-Fluorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Participants

Reaction Steps

To 1-(4-fluorobenzyl)piperazine (0.081 g, 0.416 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.165 g, 0.436 mmol) and 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.135 g, 0.457 mmol) in dichloromethane (1 mL) was added diisopropylethylamine (0.109 mL, 0.623 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated and loaded onto a silica gel column (Analogix® SF25-25) and eluted with a gradient of 5% to 100% ethyl acetate/hexanes to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.20-7.37 (m, 12H), 6.97-7.04 (m, 2H), 4.18 (s, 2H), 3.59 (t, J=4.7 Hz, 2H), 3.51 (t, J=6.5 Hz, 2H), 3.44 (s, 2H), 3.39-3.44 (m, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.38 (t, J=4.9 Hz, 2H), 2.28-2.32 (m, 2H); MS (ESI+) m/z 472 (M+H)+.

Provenance & Evidence