Mestanolone → Methyl-1-testosterone

HRID 1743348Notes

Reaction equation

HRID 1743348 reaction equation
[CH3:1][C@@:2]12[C@H:12]3[CH2:13][CH2:14][C@:15]4([CH3:22])[C@:19]([OH:21])([CH3:20])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C@H:8]1[CH2:7][C:5](=[O:6])[CH2:4][CH2:3]2.I(C1C=CC=CC=1C(O)=O)(=O)=O>>[OH:21][C@@:19]1([CH3:20])[CH2:18][CH2:17][C@H:16]2[C@H:11]3[C@H:12]([CH2:13][CH2:14][C@:15]12[CH3:22])[C@:2]1([CH3:1])[C@H:8]([CH2:7][C:5](=[O:6])[CH:4]=[CH:3]1)[CH2:9][CH2:10]3

Participants

3

Reactant 2

HCID 10633MestanoloneHCID 1087942-Iodoxybenzoic acid

Product 1

HCID 7092657Methyl-1-testosterone

Procedure

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).

Sources & evidence

ORD record
ord-35b5fc4a06974610b38f66fd2b350662
Source dataset
uspto-grants-2006_03
Patent number
US07009063B2

Reaction notes

Loading…