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N‐ Alkyl 3‐aminobut‐2‐enenitrile as a Non‐radioactive Side Product in Nucleophilic 18 F‐Fluorination
Author(s) -
Song Ruichong,
Tago Tetsuro,
Tatsuta Maho,
Shiraishi Nana,
Iwai Kumiko,
Hirano Keiichi,
Toyohara Jun,
Tanaka Hiroshi
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100723
Subject(s) - acetonitrile , nucleophile , chemistry , alkyl , medicinal chemistry , ligand (biochemistry) , fluoride , alcohol , derivative (finance) , nucleophilic addition , stereochemistry , organic chemistry , inorganic chemistry , receptor , catalysis , biochemistry , financial economics , economics
We found that acetonitrile acted as a reactant under the conventional reaction conditions for aliphatic nucleophilic 18 F‐fluorination in acetonitrile to provide the N ‐alkyl 3‐aminobut‐2‐enenitrile as one of the side products. Dimerization of acetonitrile promoted by a complex of K 2 CO 3 and K222 provided 3‐aminobut‐2‐enenitrile, which acted as nucleophile to provide N ‐alkyl amino derivatives. Based on the finding, avoiding acetonitrile in the drying of [ 18 F]fluoride as well as 18 F‐labeling enabled the preparation of 18 F‐labeled compounds containing only a small amount of the corresponding alcohol. Finally, we used an automated synthesizer to achieve an efficient phase‐tag‐assisted synthesis of 18 F‐labeled stilbene derivative as a 18 F‐labeled amyloid‐β ligand.