Dichloromethane → N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Participants

Reaction Steps

Sodium borohydride (0.37 g, 9.7 mmol) was added in portions to a stirred solution of N-[2-benzyloxy-5-(2-dibenzylamino-1-oxo-ethyl)-phenyl]-methanesulfonamide (which was obtained in Intermediate 6) (1.0 g, 1.9 mmol) in 20 mL of methanol/tetrahydrofuran (5:2) at room temperature and the resulting solution was stirred for 2 hours. Methylene chloride was added and the resulting solution was washed with aqueous sodium bicarbonate, dried over magnesium sulfate and the solvents were removed. Recrystallization from methylene chloride/hexanes gave the title compound as a crystalline solid; 1 H NMR (300 MHz, CDCl3) δ2.58 (d, J=6.7 Hz, 2 H), 2.86 (s, 2 H), 2.92 (s, 2 H), 3.55 (d, J=13.5 Hz, 2 H), 3.70 (d, J=13.5 Hz, 2 H), 4.11 (s, 1 H), 4.64 (t, J=6.7 Hz, 1 H), 5.10 (s, 2 H), 6.92 (d, J=8.5 Hz, 1 H), 7.00 (dd, J=8.5, 2.0 Hz, 1 H), 7.20-7.50 (m, 16 H), 7.89 (brs, 1 H); MS (ES) m/z: 517.1 (MH+); HRMS Calcd. for C30H32N2O4S(M+): 516.2083. Found: 516.2074.

Provenance & Evidence