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ChemicalBook CAS DataBase List Fluoxymesterone
76-43-7

Fluoxymesterone synthesis

1synthesis methods
Fluoxymesterone, 9-fluoro-11β,17β-dihydroxy-17α-methylandrost- 4-en-3-one (29.3.8), is made from 11β-hydroxy-4-androsten-3,17-dione, which is reacted with pyrrolidine to give a dieneamine (29.3.4). This undergoes a reaction with methylmagnesiumiodide, which after hydrolysis forms 11β,17β-dihydroxy-17α-methylandrost- 4-en-3-one (29.3.5). Dehydration of this compound by selective tosylation of the secondary hydroxyl group at C11 using p-toluenesulfonyl chloride and subsequent reaction with a base gives the diene (29.3.6), and the double bond at C9–C11 is transformed to an epoxide (29.3.7) by subsequent reaction with N-bromoacetamide in a wet solvent (source of HOBr), and a base. Further reaction with hydrogen fluoride results in an opening of the epoxide ring and the formation of the desired fluoxymesterone (29.3.8).

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: methanol; aq. NaOH solution
2: CH2Cl2; water; HF

References:

Herr et al. [Journal of the American Chemical Society,1956,vol. 78,p. 500]

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