Steroid-hindered 17 beta-tertiary alcohol: characterization of dehydrated compounds.
Five dehydrated compounds obtained from a tert-butyldimethylsilylchloride/imidazole or an aqueous hydrochloric acid treatment of 17 alpha-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 17 beta-tertiary alcohol.
Bydal
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Medicinal Chemistry Division, CHUL Research Center, Ste-Foy, Quebec, Canada.
Sam
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Poirier
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D002851:Chromatography, High Pressure Liquid; D004126:Dimethylformamide / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives / Q000737:chemistry*; D004965:Estrogen Antagonists / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D014867:Water
D004965:Estrogen Antagonists; D007093:Imidazoles; D014867:Water; D004958:Estradiol; C063145:N-tert-butyldimethylsilylimidazole; C029899:imidazole; D004126:Dimethylformamide; D006851:Hydrochloric Acid