Steroid-hindered 17β-tertiary alcohol: Characterization of dehydrated compounds

Article abstract of DOI:10.1016/0039-128X(96)00036-0

Five dehydrated compounds obtained from a tert- butyldimethylsilychloride/imidazole or an aqueous hydrochloric acid treatment of 17α-butyl-3-O-methyl estradiol in refluxing solvent were purified and characterized. Three compounds were obtained from a direct vicinal proton elimination, the two others from a vicinal elimination after migration of methyl-18. Depending on the treatment, the proportions of dehydrated compounds are different. In addition, a general profile of experimental conditions providing a similar mixture of dehydrated compounds was also established for this steroid-hindered 17β-tertiary alcohol.