Formaldehyde → HCID 57401546, compound

Participants

Reaction Steps

A solution of the product of Example 39B (70 mg, 0.25 mmol) in water (2 mL), was treated with formaldehyde (38% aq., 3 mL) and NaBH(OAc)3 (250 mg, 1.18 mmol; Aldrich). After stirring at room temperature for 60 h, the reaction mixture was concentrated under vacuum and purified by flash chromatography (40 g silica gel, 1:10:89 NH4OH-MeOH-CH2Cl2) to afford the title compound (57 mg, 0.20 mmol; 91% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.37-7.51 (4H, m), 7.10-7.19 (1H, m), 7.02 (1H, d, J=2 Hz), 6.85 (1H, dd, J=8, 2 Hz), 4.02 (1H, dd, J=6, 5 Hz), 3.72-3.82 (2H, m), 3.15-3.40 (4H, m), 3.03 (1H, dd, J=11, 4 Hz), 2.39 (3H, s); MS (DCl/NH3): m/z 291 (M+1)+.

Provenance & Evidence