Steroids XLIV. Synthesis and D-homoisomerization of 3β-acetoxy-6α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one
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The reactions of 16β-bromo-3β,17α-dihydroxypregn-5-en-20-dione (III) and its 3,17-diacetate (IV) with aniline have been studied. The reaction of (III) with aniline leads to the formation of the 20-anil of 16α,17α-epoxypregnenolone (V) and the reaction of (IV) with aniline to the formation of 3-acetoxy-16α-(N-acetylanilino)-17α-hydroxypregn-5-en-20-one (IX).
The hydrolysis of the diacetate (IX) with potassium carbonate in aqueous methanol has been studied. The hydrolysis is accompanied by D-homoisomerization with the formation of 16α-anilino-3β,17α-dihydroxy-17β-methyl-D-homoandrost-5-en-17a-one.
The structures and configurations of the compounds obtained (V, VI, VII, IX, X, and XI) have been shown by a series of chemical transformations and by physicochemical methods.
KeywordsAniline Hydroxy Group Diacetate Acetic Anhydride Potassium Carbonate
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- 1.G. A. Frangulyan, V. M. Potapov, V. L. Sadovskaya, L. M. Alekseeva, and N. N. Suvorov, Khim. Prirodn. Soedin.,6, 698 (1970).Google Scholar
- 5.W. Neudert and A. Röpke, Atlas of Steroid Spectra, Springer-Verlag (1965).Google Scholar
- 6.L. F. Fieser and M. Fieser, Steroids, Reinhold (1959).Google Scholar
- 8.V. A. Dubrovskii, A. A. Akhrem, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 103 (1964).Google Scholar