Bile acids. XL. Methyl 3beta, 7beta-dihydroxy-5alpha-cholanate. An example of dehydrogenation with Raney nickel

The bile acid derived from hydrogenolysis of methyl 6-oxo-3α, 7β-dihydroxy-5α-cholanate-6-ethylenethioketal with Raney nickel has been shown to be 3β, 7β-dihydroxy-5α-cholanic acid (VI). On extended reflux with Raney nickel the original C-3 hydroxyl group is dehydrogenated and the 3-oxo-derivative reduced principally to the equatorial 3β-o1. The positions and configurations of the hydroxyl groups were determined by reduction of the derived monohydroxy mono-oxo derivatives to the known monohydroxy acids. The materials (VI) has been synthesized from 3β-hydroxy-7-oxo-5α-cholanic acid by reduction with sodium and alcohol. Physical properties support the assigned structure.