Mestanolone → Methyl-1-testosterone

Participants

Reaction Steps

In yet another aspect of the present invention, mestanolone is reacted with IBX to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one. The 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one is reacted with osmium tetroxide and N-methylmorpholine N-oxide to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one. The 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one is reacted with sodium metaperiodate to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid. Oxandrolone is then formed from the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid by reacting the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid with sodium borohydride followed by an acid treatment comprising addition of hydrochloric acid.

Provenance & Evidence