Fluoro norcholesterol analogues. Synthesis of 6 beta-(2'-fluoro) ethyl-19-norcholest-5(10)-en-3 beta-ol
AbstractAbstract
[en] A synthetic route for labelling 6 beta-(2'-fluoro)ethyl-19-norcholest-5(10)-en-3 beta-ol (VII) with fluorine-18 was developed to evaluate the potential utility of VII as an adrenal imaging agent. 6 beta-p-Toluene-sulphonyloxymethyl-19-norcholest-5(10)-en-3 beta-ol acetate (I) was converted to the 6 beta-(2'-hydroxy)ethyl (VI) in a five-step process. The treatment of VI with N-N-diethyl (2-chloro-1,1,2,-trifluoroethyl)amine in methylene chloride and subsequent hydrolysis with base gave the required VII. Iodination of VI with triphenoxymethylphosphonium iodide followed by alkaline hydrolysis gave the 6 beta-(2'-iodo)ethyl (IX) which, on treatment with silver fluoride in acetonitrile, furnished the 6 beta-(2'-fluoro)ethyl (VII). Excellent conversion of the 6-beta-(2'-p-toluenesulphonyloxy)-ethyl (X) into VII was also achieved by heating with potassium fluoride for 2 hr in diethylene glycol in 76% yield, which is a readily applicable method for labelling with fluorine-18
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Journal Article
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Steroids; ISSN 0039-128X; ; v. 39(5); p. 585-593
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BETA DECAY RADIOISOTOPES, BETA-PLUS DECAY RADIOISOTOPES, BODY, CHEMICAL REACTIONS, CHEMISTRY, COUNTING TECHNIQUES, DECOMPOSITION, DIAGNOSTIC TECHNIQUES, DRUGS, ENDOCRINE GLANDS, ENERGY LEVELS, FLUORINE ISOTOPES, GLANDS, HOURS LIVING RADIOISOTOPES, ISOTOPES, LIGHT NUCLEI, MATERIALS, NUCLEI, ODD-ODD NUCLEI, ORGANIC COMPOUNDS, ORGANS, RADIOACTIVE MATERIALS, RADIOISOTOPE SCANNING, RADIOISOTOPES, SOLVOLYSIS, SYNTHESIS
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