HCID 11001884, compound → HCID 12134979, compound

Participants

Reaction Steps

To a solution of the known 3-hydroxy-2-(1-methyl-2-propenyl)estra-1,3,5(10)-trien-17-one (ref. Patton, 1962; Chemical Abstracts Registry Number [98543-85-2], 30 mg, 0.093 mmol) dissolved in 10 mL of anhydrous ethanol was added 20 mg of 5% Pd/C. The reaction flask was shaken under 2.7 atm. of hydrogen for 3 h. The reaction mixture was then filtered and the catalyst was washed with ethanol. After solvent removal, the crude product was purified by chromatography (silica gel eluted with 12.5% ethyl acetate in hexanes) and then recrystallized from methylene chloride-hexanes to give 20 mg of pure product: m.p. 186-187° C.; 1H NMR(CDCl3) δ0.85-0.90 (m, 3H, CH3), 0.91 (s, 3 h CH3), 1.20-1.24 (m, 3H, CH3), 2.81-2.89 (m, 2H, CH2), 6.51 (s, 1H, Ar—H), 7.06 (s, 1H, Ar—H); 13C NMR(CDCl3) δ12.17, 13.75, 20.44, 21.46, 25.93, 28.91, 29.83, 31.49, 33.87, 35.81, 38.33, 44.05, 48.01, 50.24, 115.37, 123.99, 124.17, 130.86, 131.88, 134.78, 157.267, 221.79.

Provenance & Evidence