3,17beta-Bis(benzyloxy)-11-(2-propenyl)estra-1,3,5(10),9(11)-tetraene → (4S,5R)-1-[(2R,9Z)-11-[3,17beta-bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one

Participants

Reaction Steps

3,17β-Bis(benzyloxy)-11-(2-propenyl)estra-1,3,5(10),9(11)-tetraene (491 mg, 1.00 mmol) and the (4S,5R)-3,4-dimethyl-1-[(2R)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoyl]-5-phenylimidazolidin-2-one (1.18 g, 2.00 mmol) prepared in Example 36 were dissolved in anhydrous dichloromethane (10 ml) at room temperature under nitrogen atmosphere, mixed with benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium (41 mg, 0.05 mmol), and then heated under reflux followed by stirring for 6 hours under nitrogen atmosphere. After cooling, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel flash chromatography (eluent: ethyl acetate/n-hexane=3/7) to give a mixture of (4S,5R)-1-{(2R,9E)-11-[3,17β-bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one and (4S,5R)-1-{(2R,9Z)-11-[3,17β-bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one (664 mg, Yield 63%).

Provenance & Evidence