Benzophenone → HCID 45275495, compound

Participants

Reaction Steps

A mixture of 1-(2-(4-aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one (Example 87B, 0.1 g, 0.25 mmol) and benzophenone (0.056 g, 0.3 mmol) is stirred in dichloromethane (3 mL) with titanium(IV) isopropoxide (0.012 g, 0.4 mmol) for 3 hours. The reaction mixture was then diluted with methanol (10 mL) and sodium borohydride (0.4 g, 0.4 mmol) was added. The mixture was stirred at ambient temperature for 16 hours and then concentrated. The residue was partition in ethyl acetate/H2O (100 mL/20 mL). The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.26-7.38 (m, 16H), 7.15-7.24 (m, 4H), 4.99 (s, 1H), 4.36-4.44 (m, 1H), 4.21 (s, 2H), 3.70-3.77 (m, 1H), 3.48 (t, J=6.4 Hz, 2H), 2.93-3.03 (m, 1H), 2.69-2.79 (m, 1H), 2.61-2.69 (m, 3H), 1.89-2.00 (m, 2H), 1.77-1.89 (m, 2H), 1.24-1.41 (m, 3H); MS (ESI+) m/z 558 (M+H)+.

Provenance & Evidence