Stenbolone

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Stenbolone
Stenbolone.png
Names
IUPAC name
(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Other names
Deacetylanatrofin; 17β-Hydroxy-2-methyl-5α-androst-1-en-3-one
Identifiers
5197-58-0 YesY
Jmol-3D images Image
PubChem 234454
Properties
C20H30O2
Molar mass 302.45 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Stenbolone is an anabolic steroid. It is structurally similar to 1-testosterone.

Synthesis[edit]

The route used to prepare the unsaturated 2 methyl androgen stenbolone provides yet a further illustration of the propensity for the formation of enolates at the 2 position.[1]

Preparation of the acetate ester of stenbolone

Thus reaction of dihydrotestosterone acetate with formaldehyde and dimethylamine gives the Mannich product. Hydrogenolysis of that product gives the 2-methyl derivative via elimination of dimethylamine. Bromination of the ketone leads to the 2-bromo derivative. Dehydrobromination by means of lithium carbonate in dimethyl formamide (DMF) affords the androgen stenbolone acetate.

References[edit]

  1. ^ U.S. Patent 3,361,773 Wiechert Rudolf; (1968). Schering AG, Berlin