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ChemicalBook CAS DataBase List 17-Methyltestosterone
58-18-4

17-Methyltestosterone synthesis

10synthesis methods
Methyltestosterone, 17β-hydroxy-17α-methylandrost-4-en-3-one (29.1.7), is also synthesized from androstenolone by reacting it with methylmagnesiumiodide, forming the corresponding tertiary alcohol (29.1.6), and subsequent oxidation of the hydroxyl group at C3 to a ketone using chromium (VI) oxide. Simultaneous isomerization of the double bond takes place under the reaction conditions, giving the desired methyltestosterone (29.1.7).

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Yield:-

Steps:

Multi-step reaction with 4 steps
1: hydroxylamine hydrochloride
2: pyridine; trichlorophosphate / N,N-dimethyl-formamide
3: sodium hydroxide; sodium tetrahydroborate
4: manganese(IV) oxide

References:

CN106397521,2017,A

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