Sodium borohydride → HCID 66652033, compound

Participants

Reaction Steps

Combine 1-[6-hydroxy-10-(4-hydroxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-ethanone (0.027 g, 0.08 mmol), NaBH4 (0.010 g, 0.24 mmol), and ethanol (4 mL), and reflux under nitrogen atmosphere. After 72 hours, cool the reaction to room temperature, concentrate, and add ethyl acetate. Wash with sat ammonium chloride solution (aq), then brine, and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to yield the titled compound (0.003 g, 11%) as a white solid. 1H NMR (d-methanol): 7.62 (d, 1H, J=8.4 Hz), 7.15 (m, 2H), 6.84 (s, 1H), 6.78 (m, 2H), 6.64 (m, 1H), 3.94 (m, 1H), 3.49 (d, 1H, J=11.5 Hz), 3.33 (m, 1H), 3.13 (s, 1H), 2.91 (dd, 1H, J=11.5, 3.5 Hz), 2.47 (m, 1H), 1.86 (m, 1H), 1.68 (m, 1H), 1.52 (m, 1H), 1.30 (m, 3H), 1.05 (m, 4H), 0.83 (d, 2H, J=6.2 Hz); MS m/z 337 (M−1).

Provenance & Evidence