Fluoro norcholesterol analogues. Synthesis of 6 beta-(2'-fluoro) ethyl-19-norcholest-5(10)-en-3 beta-ol

Journal Article · Sat May 01 00:00:00 EDT 1982 · Steroids; (United States)

DOI:https://doi.org/10.1016/0039-128X(82)90058-7· OSTI ID:6376329

Kobayashi, T; Maeda, M; Haradahira, T; Kojima, M

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.

• Research Organization: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
• OSTI ID: 6376329
• Journal Information: Steroids; (United States), Vol. 39:5
• Country of Publication: United States
• Language: English

Related Subjects

62 RADIOLOGY AND NUCLEAR MEDICINE
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
FLUORINE 18
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
CHEMICAL PREPARATION
ADRENAL GLANDS
ALKALINE HYDROLYSIS
BIOCHEMISTRY
IMAGES
ISOBARIC ANALOGS
RADIOPHARMACEUTICALS
SCINTISCANNING
STEROIDS
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
HYDROLYSIS
ISOTOPES
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANS
RADIOISOTOPE SCANNING
RADIOISOTOPES
SOLVOLYSIS
SYNTHESIS
550601* - Medicine- Unsealed Radionuclides in Diagnostics
400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials