Acetic Acid → HCID 67340191, compound

Participants

Reaction Steps

A solution of compound 119 (0.75 g, 2.926 mmol) in 1,2-dichloroethane (20 mL) was treated with AcOH (0.16 mL, 2.926 mmol), isopropyl amine (0.25 mL, 2.926 mmol), NaBH(OAc)3 (0.93 g, 4.390 mmol) at room temperature and stirred for over night (16 h). The reaction was basified with 2 N NaOH (25 mL) and product was extracted into ethyl acetate (3×50 mL). The combined ethyl acetate layer washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 139 (0.636 g, 73%) as a semi-solid. 1H NMR (DMSO-d6) δ 0.99 (d, 6H, J=6.0 Hz), 1.36-1.47 (m, 1H), 1.89-1.97 (m, 2H), 2.45-2.56 (m, 2H), 2.81-2.89 (m, 1H), 2.91-2.99 (m, 1H), 3.16 (brs, 1H), 6.14 (brs, 1H), 7.80 (s, 1H), 7.88 (dd, 1H, J=2.1, 9.0 Hz), 7.95 (d, 1H, J=9.0 Hz), 8.30 (d, 1H, J=2.1 Hz), 11.83 (brs, 1H); ESI-MS (m/z, %) 300 (MH+, 100), 241 (35).

Provenance & Evidence