Sodium borohydride → HCID 18595675, compound

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Reaction Steps

300 mg. of 3,16α-diacetoxy-6β-ethoxycarbonylmethyl-1,3,5(10)-estratrien-17-one is dissolved in 11 ml. of methanol and gradually combined at +5°C. with 0.17 g. of NaBH4 in 9 ml. of methanol. After allowing the mixture to stand for 20 hours at room temperature, it is concentrated and stirred into water which contains hydrochloric acid. The reduction product is taken up in ethyl acetate, the solution is washed neutral, dried, and evaporated. By preparative thin-layer chromatography, 330 mg. of crude product yields 16α-acetoxy-6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol, m.p. 170.5°-171.5°C. and 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,16α,17β-triol, m.p. 192.5°-193°C.

Provenance & Evidence