Amino Steroids ‐ Further Studies with Conanine and Heteroconanine Systems
- 1 January 1982
- journal article
- Published by Wiley in Bulletin des Sociétés Chimiques Belges
- Vol. 91 (1) , 67-73
- https://doi.org/10.1002/bscb.19820910110
Abstract
Treatment of any of the three following products, heteroconanol methiodide (3′), conanol methiodide (4′) or 18‐dimethylamino‐5α‐pregn‐20‐en‐3β‐ol (1), with a large excess of potassium hydroxide in hot ethylene glycol affords rapidly a mixture of heteroconanol (3, ), conanol (4, ) and the Δ 17(20) isomer of 1 (2,). The presence of such an isomer has not yet been reported in analogous reactions of related compounds. The Hofmann elimination product 1 is thought to be involved as an equilibrium intermediate in each of the three reactions; its isomer 2 should be formed by base‐catalyzed isomerization and not by eliminative ring fission.Keywords
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