Ring opening of epoxides with [F]FeF species to produce [F]fluorohydrin PET imaging agents

A simple technique for the preparation of [ 18 F]HF has been developed and applied to the generation of an [ 18 F]FeF species for opening sterically hindered epoxides. This method has been successfully employed to prepare four drug-like molecules, including 5-[ 18 F]fluoro-6-hydroxy-cholesterol, a p...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-05, Vol.55 (45), p.6361-6364
Main Authors: Verhoog, Stefan, Brooks, Allen F, Winton, Wade P, Viglianti, Benjamin L, Sanford, Melanie S, Scott, Peter J. H
Format: Article
Language:English
Subjects:
Cholesterol
Epoxy Compounds - chemistry
Fluorides - chemistry
Fluorine isotopes
Fluorine Radioisotopes
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Imaging
Iron - chemistry
Positron emission
Positron-Emission Tomography
Radiopharmaceuticals - chemistry
Ring opening
Tomography
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Summary:A simple technique for the preparation of [ 18 F]HF has been developed and applied to the generation of an [ 18 F]FeF species for opening sterically hindered epoxides. This method has been successfully employed to prepare four drug-like molecules, including 5-[ 18 F]fluoro-6-hydroxy-cholesterol, a potential adrenal/endocrine PET imaging agent. This easily automated one-pot procedure produces sterically hindered fluorohydrin PET imaging agents in good yields and high molar activities. This report describes a simple technique for the preparation of [ 18 F]HF and its application to the generation of an [ 18 F]FeF species for opening sterically hindered epoxides. This easily automated one-pot procedure has been successfully employed to prepare four drug-like molecules in good yields and high molar activities, including 5-[ 18 F]fluoro-6-hydroxy-cholesterol.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02779c