Mestanolone → Methyl-1-testosterone

HRID 1743349Notes

Reaction equation

HRID 1743349 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 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.

Sources & evidence

ORD record
ord-631dd90300dd4aa2b07c1d11e9c849e4
Source dataset
uspto-grants-2006_03
Patent number
US07009063B2

Reaction notes

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