Formaldehyde → HCID 67248586, compound

Participants

Reaction Steps

To a solution of Example 226 (50 mg, 0.229 mmol) in a pH 4 buffer solution (10 mL, made from 48 g acetic acid and 30.5 g sodium acetate in 1 L methanol) was added formaldehyde (36% solution, 13.8 mg, 0.46 mmol) and macroporous-cyanoborohydride resin (0.32 g, 0.69 mmol). The reaction was allowed to stir for 2 hours before the macroporous-cyanoborohydride resin was removed by filtration, and the solution concentrated. The concentrate was basified to pH=10 with NaOH (1 M aqueous), and the product was extracted with ethyl acetate. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.69-6.86 (m, 3H), 4.24-4.37 (m, 1H), 4.06-4.16 (m, 1H), 2.99-3.18 (m, 3H), 2.56-2.68 (m, 1H), 2.46-2.55 (m, 1H), 2.18-2.29 (m, 1H), 2.21 (s, 3H), 2.02-2.16 (m, 1H), 2.09 (s, 3H), 1.79-1.99 (m, 2H); MS (DCI+) m/z 233 (M+H)+.

Provenance & Evidence