Methylamine → HCID 86591331, compound

Participants

Reaction Steps

Compound 4 (2.29 g, 6.56 mmol) was dissolved in the mixture of THF (50 mL) and MeOH (50 mL). To this solution was added the aqueous solution of methylamine (40%, wt, 20 mL), the reaction mixture was stirred at room temperature under nitrogen for 12 h. Sodium borohydride (1.00 g, 26.3 mmol) was added, and stirred for 30 min. After removal of the solvent in vacuo, the resulting residue was dissolved in ethyl acetate (100 mL), washed with water (3×50 mL), and dried over MgSO4. Solvent evaporation gave a crude product, which was purified on a silica gel column, eluting with MeOH/CH2Cl2 (1/2), giving compound 5 as a yellow solid (2.00 g, 83%). 1H NMR (CDCl3) δ 8.44-8.39 (m, 4H), 7.56-7.53 (m, 4H), 5.51 (s, 2H), 4.71 (s, 2H), 2.69 (s, 3H), 2.46 (s, 3H), 1.55 (s, 9H). 13C NMR (CDCl3) δ 155.6, 132.5, 131.0, 130.0, 125.8, 125.7, 125.4, 125.3, 124.9, 79.7, 47.8, 42.6, 36.9, 31.6, 28.6. IR (cm−1): 1686. HRMS (FAB) calcd for C23H28N2O2 (M+) 364.2151, found 364.2159. Anal. calcd for C23H28N2O2: C, 75.79; H, 7.74; N, 7.69. Found: C, 75.64; H, 7.71; N, 7.53.

Provenance & Evidence