Diisopropylethylamine → HCID 67360202, compound

Participants

Reaction Steps

To 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.103 g, 0.334 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.155 g, 0.408 mmol) and 2-phenylmorpholine (0.074 g, 0.371 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.097 mL, 0.556 mmol), and the reaction mixture was stirred at room temperature. After stirring overnight, the reaction was directly loaded onto a silica gel column (Analogix®, SF15-12), and the product was eluted with a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes with a flow rate of 30 mL/minute. The product eluted with a more polar impurity. The product was rechromatographed over silica gel (Analogix®, SF15-12), and the title compound was eluted with a gradient of 0.4% to 7.5% methanol/dichloromethane over 20 minutes with a flow rate of 30 mL/minute. 1H NMR (300 MHz, CDCl3) δ ppm 7.18-7.40 (m, 15H), 4.37-4.68 (m, 3H), 3.98-4.17 (m, 2H), 3.32-3.85 (m, 6H), 2.64-2.70 (m, 2H), 1.82-1.88 (m, 2H); MS (ESI+) m/z 455 (M+H)+.

Provenance & Evidence