Acetic Acid → 2-Methoxy-6a-methyl-4b,6,6a,7,8,8a,9,9b,10,11-decahydro-5H-cyclopropa[1,5]cyclopenta[1,2-a]phenanthren-7-ol

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Reaction Steps

400 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17-one dissolved in 300 ml of methanol are mixed with 380 mg of sodium borohydride at 0° C. and set aside overnight at room temperature. Subsequently the mixture is reduced to half its volume in vacuum and poured into cold aqueous acetic acid. The precipitate is dried, and preparative layer chromatography on silica gel (mobile phase: benzene/acetone 3:2) yields 90 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17β-ol and 210 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17α-ol. Flash point 117° to 119° C., specific optical rotation: [α]D25 +104.0° (c=1; CHCl3).

Provenance & Evidence