Mestanolone → Methyl-1-testosterone

HRID 1006196Notes

Reaction equation

HRID 1006196 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>C1(C)C=CC=CC=1.CS(C)=O>[CH3:20][C@:19]1([OH:21])[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

4

Reactant 2

HCID 10633Mestanolone2×HCID 1087942-Iodoxybenzoic acid

Product 1

HCID 7092657Methyl-1-testosterone

Reagents, catalysts & solvents 1

HCID 22340214Dimethylsulfoxide tolueneSolvent

Conditions

Temperature
67.5 °C

Procedure

A mixture of mestanolone (55.3 g, 0.182 mol) and IBX (76.5 g, 0.273 mol, 1.5 eq.) in 1800 ml toluene:DMSO (2:1) was heated at 65-70° C. for 48 h after which time the beginning clear solution turned into a suspension. TLC (thin layer chromatography) indicated the disappearance of starting mestanolone and the appearance of the desired product and two by-products. After cooling to RT (room temperature), the reaction mixture was filtered on a frit and solid washed with ethyl acetate (2×200 ml). The filtrate was diluted with 1000 ml of ethyl acetate and the resulting organic phase was washed with 1000 ml each of 5% NaHCO3, water, and brine. After drying over sodium sulfate, removal of the solvents on a rotavapor gave ˜56.0 g of a crude products mixture containing the required product (i.e., 17α-methyl-17β-hydroxy-5α-androst-1-en-3-one) along with two minor by-products.

Sources & evidence

ORD record
ord-e991daed98e449a581463490e328ac3f
Source dataset
uspto-grants-2004_09
Patent number
US06787659B2

Reaction notes

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