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

Ivana Kuzminac | Zendy; Olivera R. Klisurić | Zendy; Andrea Nikolić | Zendy; Marija N. Sakač | Zendy

Open Access

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

Author(s) -

Ivana Kuzminac,

Olivera R. Klisurić,

Andrea Nikolić,

Marija N. Sakač

Publication year - 2018

Publication title -

facta universitatis - series physics chemistry and technology

Language(s) - English

Resource type - Journals

eISSN - 2406-0879

pISSN - 0354-4656

DOI - 10.2298/fupct1802219k

Subject(s) - perchloric acid , chemistry , reagent , tetrahydrofuran , solvent , derivative (finance) , organic chemistry , medicinal chemistry , financial economics , economics

Reaction conditions variation and its influence on the reaction of 3?- acetoxy-17-oxa-17a-homoandrost-5-en-16-one with in situ generated hypobromous acid was investigated. Hypobromous acid was generated from N-bromoacetamide or Nbromosuccinimide 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. 6?-Bromo-5?- hydroxy 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.

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