Phthalimide → Methyl 4-{3-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate

Participants

Reaction Conditions

Reaction Steps

1.5 g of methyl 4-[7,12-Dihydroxy-3-(2-hydroxyethoxy)-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate, 950 mg of triphenylphosphine and 550 mg of phthalimide are warmed to 45° C. in 26 ml of THF and 1.14 ml of diethyl azodicarboxylates are added dropwise at this temperature. The reaction mixture is stirred at 45° C. for 2 hours, then poured into 200 ml of a semiconcentrated aqueous NaHCO3 solution and extracted 3 times using 200 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using t-butyl methyl ether (MTB) yields 1.76 g of a viscous oil

Provenance & Evidence