Acetic Acid → HCID 25122337, compound

Participants

Reaction Steps

To a stirred solution of compound 8 (56.74 mg, 0.136 mmol) in DMF (10 mL) was added benzaldehyde (21.65 mg, 0.204), MP-triacetoxyborohydride (2.70 mmol/g, 302 mg, 0.816 mmol), and acetic acid (24.5 mg, 0.408 mmol). It was stirred at room temperature overnight. The resin was removed by filtration. The solvent was removed and chromatography on silica gel afforded compound 9 (46.0 mg, 93.6). 1H NMR (CD3OD, 400 MHz) δ 8.19 (d, 1H, J=5.5 Hz), 8.09 (d, 1H, J=7.5 Hz), 7.20-7.35 (m, 6H), 6.81 (d, 1H, J=7.5 Hz), 3.62-3.71 (m, 2H), 3.55 (s, 2H), 2.75 (s, 3H), 2.45-2.70 (m, 10H). LCMS (EI) m/z 362 (M+1).

Provenance & Evidence