Oxandrolone → Methyl-1-testosterone

HRID 1743347Notes

Reaction equation

C[C@@]12[C@](O)(C)CC[C@H]1[C@@H]1CC[C@H]3CC(=O)OC[C@]3(C)[C@H]1CC2.[CH3:23][C@@:24]12[C@H:34]3[CH2:35][CH2:36][C@:37]4([CH3:44])[C@:41]([OH:43])([CH3:42])[CH2:40][CH2:39][C@H:38]4[C@@H:33]3[CH2:32][CH2:31][C@H:30]1[CH2:29][C:27](=[O:28])[CH2:26][CH2:25]2>>[OH:43][C@@:41]1([CH3:42])[CH2:40][CH2:39][C@H:38]2[C@H:33]3[C@H:34]([CH2:35][CH2:36][C@:37]12[CH3:44])[C@:24]1([CH3:23])[C@H:30]([CH2:29][C:27](=[O:28])[CH:26]=[CH:25]1)[CH2:31][CH2:32]3

Participants

Reactant 2

HCID 5878Oxandrolone

HCID 10633Mestanolone2×

Product 1

HCID 7092657Methyl-1-testosterone

Procedure

The present invention relates to a process for the synthesis of oxandrolone from mestanolone. In one aspect of the present invention, a process is provided comprising the steps of: (a) oxidizing mestanolone 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 1≢, 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.

Workup

customIn one aspect of the present invention, a process is provided

Sources & evidence

ORD record: ord-c2b0d2f57084408c8394e893a2bc288c
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07009063B2

Reaction notes

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