Mestanolone → Methyl-1-testosterone

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Reaction Steps

In a further aspect of the present invention, mestanolone is oxidized using IBX to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one. The 17-hydroxy-17α-methyl-5α-androst-1-en-3-one is hydroxylated using osmium tetroxide to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one. The 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one is cleaved using sodium metaperiodate to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid. The 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid is then reduced using sodium borohydride followed by an acid treatment to form oxandrolone.

Provenance & Evidence