5.alpha.-Androstan-3-one, 17.beta.-hydroxy-2-(hydroxymethylene)-

Uses

4,5a-Dihydro-2-(hydroxymethylene)testosterone is an urinary metabolite of stanozolol (S684500).

Definition

ChEBI: 4,5alpha-Dihydro-2-(hydroxymethylene)testosterone is a 3-oxo-5alpha-steroid.

Synthesis

4,5α-dihydro-2-(hydroxymethylene)testosterone (oxystanolone) is obtained by reacting 2-Hydroxymethylene-androstan-17β-((tetrahydro-2H-pyran-2-yl)oxy)-3-one with pyridinium tosylate.
Procedure: To a solution of 0.95 g intermediate (2) in 55 ml of the solvent mixture tetrahydrofuran/methanol/water 7:2:1 pyridinium tosylate (1.15 g dissolved in 20 ml tetrahydrofuran/methanol/water 7:2:1) was added at room temperature. Subsequently, this was followed by 8 h stirring at 50°C. Monitoring via TLC still shows remaining starting material. After evaporation of all solvents, the crude product was chromatographed on silica gel by using hexane-ethyl acetate (8:2). 0.385 g of 5 was obtained as a colorless solid (52%).

Raw materials

Preparation Products