77210-51-6Relevant academic research and scientific papers
Nucleophilic Fluorination and Radiofluorination via Aziridinium Intermediates: N-Substituent Influence, Unexpected Regioselectivity, and Differences between Fluorine-19 and Fluorine-18
Médoc, Marie,Sobrio, Franck
, p. 10086 - 10097 (2015/11/03)
The efficient dehydrofluorination and radiofluorination of N,N-disubstituted-β-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 18F-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 °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 [18F]-fluorodeprenyl. This method involving nucleophilic radiofluorination at RT was successfully applied to the radiolabeling of [18F]-2-fluoroethylamines in which the influence of the N-substituent was also observed.
SYNTHESIS OF SIDE-CHAIN MONOFLUORINATED AMPHETAMINES
Coutts, R. T.,Benderly, A.,Mak, A. L. C.
, p. 277 - 284 (2007/10/02)
R- and S-2-Amino-3-fluoro-1-phenylpropane were prepared in approximately 50percent yields by the action of HF-pyridine on R- and S-2-bezylaziridene, (+/-)-2-Amino-3-fluoro-1-(4-chlorophenyl)propane was similarly prepared from (+/-)-2-(4-chlorobenzyl)aziri
