Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10086-10097Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01714
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- Conseil Regional de Basse-Normandie (Lower-Normandy Council, France)
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The efficient dehydrofluorination and radiofluorination of NN-disubstitated-beta-aminoalcohols through an anchimeric-assisted mechanism was developed. An investigation into the influence of N-substituents on the ring opening of the aziridinium intermediate indicated differences in the isomeric ratio and the yields of fluorinated products obtained from N,N-disubstituted-phenylalaninol. This influence was substantial for F-18-radiofluorination, with yields varying from 0 to 71% at room temperature (RT). Although no significant effects were observed in the fluorine-19 chemistry when the reaction was heated to 90 degrees C, considerable changes appeared during radiofluorination. In the latter case, the radiochemical yields increased, and degradation of the 2-fluoro-propan-1-amine isomer (b) occurred, leading to a regiospecific reaction in the radiolabeling of [F-18]-fluorodeprenyl. This method involving nucleophilic radiofluorination at RT was successfully applied to the radiolabeling of [F-18]-2-fluoroethylamines in which the influence of the N-substituent was also observed.
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