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Deoxyradiofluorination Reaction from β‐Hydroxy‐α‐aminoesters: an Entry to [ 18 F]Fluoroaminoesters under Mild Conditions
Author(s) -
Morlot Marine,
Gourand Fabienne,
Perrio Cécile
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900300
Subject(s) - chemistry , regioselectivity , fluoride , ring (chemistry) , medicinal chemistry , alcohol , reaction conditions , base (topology) , organic chemistry , catalysis , inorganic chemistry , mathematical analysis , mathematics
We report the conversion of β‐hydroxy‐α‐aminoesters derived from serine, α‐methylserine or β‐phenylserine to the corresponding [ 18 F]fluorinated α or β‐aminoesters by deoxyradiofluorination using [ 18 F]fluoride. The method involved the ring opening of an aziridinum intermediate formed in situ in the presence of a base after activation of the alcohol function with triflic anhydride. The overall process was carried out at room temperature. Both the efficiency and the regioselectivity of the reaction were found to be dependent on the starting substrates. [ 18 F]Fluoroaminoesters were obtained in radiochemical yields ranging from 10–75 %. No improvement was observed for reactions carried out under heating.