Acetic Acid → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

Participants

Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthren-9-carboxylic acid methyl ester (10.06 g, 26.6 mmol), 10% Pd—C (1.014 g), acetic acid (100 mL), methanol (150 mL), and ethyl acetate (150 mL), and stir under 100 psi of hydrogen atmosphere at 50° C. After 18 hours, filter reaction through Celite using ethyl acetate and concentrate to yield the titled compound (9.97 g, 99%) as a white solid. TLC Rf=0.25 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.28 (m, 1H), 7.22 (d, 2H, J=8.8 Hz), 6.98 (d, 1H, J=2.2 Hz), 6.84 (d, 2H, J=8.8 Hz), 6.80 (d, 1H, J=2.6 Hz), 4.33 (d, 1H, J=7.9 Hz), 3.86 (s, 3H), 3.82 (s, 3H), 3.55 (m, 1H), 3.51 (s, 3H), 3.06 (m, 1H), 2.36 (m, 2H), 1.78 (m, 3H), 1.38 (m, 4H).

Provenance & Evidence