Acetic Acid → HCID 57474466, compound

Participants

Reaction Steps

A solution of compound 131 (0.2 g, 0.765 mmol) in dry methanol (5 mL) was treated with formaldehyde (0.07 mL, 0.918 mmol, 37% in water), AcOH (0.1 mL, 1.913 mmol) and NaBH3CN (0.057 g, 0.918 mmol) at 0° C. The resulting mixture brought to room temperature and stirred for 3 h. The reaction was basified with 1 N NaOH (25 mL) and product was extracted into ethyl acetate (2 25 mL). The combined ethyl acetate layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:99 to 1:9) to obtain compound 132 (0.2 g, 95%) as a yellow solid. mp 94-96° C.; 1H NMR (DMSO-d6) δ 2.32 (s, 3H), 2.48-2.63 (m, 1H), 2.78-2.87 (m, 1H), 3.03-3.12 (m, 1H), 3.38-3.48 (m, 1H), 5.45 (d, 1H, J=48.9 Hz), 6.48-6.50 (m, 1H), 7.58 (d, 1H, J=8.7 Hz), 7.75 (s, 1H), 8.03 (dd, 1H, J=2.1, 9.0 Hz), 8.68 (d, 1H, J=2.1 Hz), 11.96 (s, 1H) ESI-MS m/z (%): 276 (MH+, 100).

Provenance & Evidence