Sodium borohydride → 3alpha-Hydroxy-17beta-methoxy-5alpha-androstane

Participants

Reaction Steps

Sodium borohydride (0.37 gms.) is added to a mixture of 17β-methoxy-5α-androstan-3-one (3 gms.) and isopropylalcohol (95%, 35 ml.). The mixture is stirred at 20°-25° for one hour and then is concentrated to dryness. The residue is column chromatographed on a size C prepacked Merck silica gel column. Elution was performed with ethyl acetate:cyclohexane, 10:90. 6 Ml. fractions are collected. The appropriate fractions (TLC) are combined and concentrated to dryness. The residue is recrystallized from isopropyl ether to give 3α-hydroxy-17β-methoxy-5α-androstane, m.p. 164°-167°; IR (mull) 3290, 3220, 1120, 1110, 1005 cm-1 ; NMR (CDCl3) 0.72, 0.76, 0.9-2.0, 3.21, 3.3, and 4.01 δ and 3β-hydroxy-17β-methoxy-5α-androstane, m.p. 150°-152°; NMR (CDCl3) 0.75-2.0, 3.25, 3.37 and 3.6 δ.

Provenance & Evidence