Acetic Acid → HCID 67340348, 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), n-propylamine (0.24 g, 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 was 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 133 (0.58 g, 66%) as a brown semi-solid. 1H NMR (DMSO-d6) δ 0.89 (t, 3H, J=7.2 Hz), 1.37-1.51 (m, 4H), 1.91-2.00 (m, 2H), 2.44-2.57 (m, 4H), 2.68-2.76 (m, 1H), 6.14 (s, 1H), 7.80 (s, 1H), 7.86-7.97 (m, 2H), 8.30 (d, 1H, J=2.1 Hz), 11.82 (brs, 1H); ESI-MS (m/z, %) 300 (MH+, 100).

Provenance & Evidence