Mestanolone → Methyl-1-testosterone

Participants

Reaction Steps

In another aspect of the present invention, a process is provided for the production of oxandrolone comprising the steps of: (a) oxidizing mestanolone using o-iodoxybenzoic acid (IBX) to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one; (b) hydroxylating the 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one; (c) cleaving the 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid; and (d) reducing the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid to form oxandrolone. At least two by-products are formed in step (a) that are non-reactive to steps (b) and (c).

Provenance & Evidence