Investigation of reaction conditions on synthesis of steroidal bromohydrin and structural analysis of novel 6α-brom-5β-hydroxy derivative

Abstract

Reaction conditions variation and its influence on the reaction of 3βacetoxy-17-oxa-17a-homoandrost-5-en-16-one with in situ generated hypobromous acid was investigated. Hypobromous acid was generated from N-bromoacetamide or N-bromosuccinimide and perchloric acid, and as solvent dioxane, dimethoxyethane or tetrahydrofuran were used. After a series of experiments, it was determined that the number of the reaction products depends on the reagent used, solvents, perchloric acid concentration and the presence/absence of daylight. It has also been found that the yields of certain compounds depend also on the reaction time and temperature. 6α-Bromo-5βhydroxy derivate is obtained by usage of NBA and 0.28 M perchloric acid in dioxane on daylight. Its structure was confirmed by NMR and X-ray crystal structure analysis.