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Issue 0, 1968
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Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes

Abstract

Condensation of 2α,3α- and 2β,3β-epoxy-5α-androstanes with secondary cyclic amines gives 2β-amino-3α-ols and 3α-amino-2β-ols respectively; reaction of a 2β-bromo-3α-hydroxy-5α-androstane with the same cyclic amines gives the 2α,3α-epoxide in contrast to the 3α-bromo-2β-hydroxy-isomer, which undergoes substitution without inversion to give the corresponding 3α-amino-2β-ol. The mechanisms of these reactions are discussed. The preparation of 2-morpholino-5α-androst-1-ene-3,17-dione is also described.

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Article type: Paper
DOI: 10.1039/J39680001134
J. Chem. Soc. C, 1968, 1134-1140

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    Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes

    C. L. Hewett and D. S. Savage, J. Chem. Soc. C, 1968, 1134
    DOI: 10.1039/J39680001134

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