N-Alkyl 3‐aminobut‐2‐enenitrile as a Non‐radioactive Side Product in Nucleophilic 18F‐Fluorination
N-Alkyl 3‐aminobut‐2‐enenitrile as a Non‐radioactive Side Product in Nucleophilic 18F‐Fluorination
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N-烷基 3-氨基丁-2-烯腈作为亲核 18F-氟化反应中的非放射性副产物
DOI：
10.1002/slct.202100723
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发表时间：
2021
期刊：
影响因子：
2.1
通讯作者：
Tanaka Hiroshi
中科院分区：
文献类型：
--
作者：
Song Ruichong;Tago Tetsuro;Tatsuta Maho;Shiraishi Nana;Iwai Kumiko;Hirano Keiichi;Toyohara Jun;Tanaka Hiroshi
我们发现，在常规的反应条件下，乙腈作为反应物，在乙腈中的脂肪族亲核18 F-酰基，提供N-烷基3-氨基丁-2-烯腈作为副产物之一。在K2 CO 3和K222配合物的作用下，乙腈发生二聚反应生成3-氨基丁-2-烯腈，后者作为亲核试剂生成N-烷基氨基衍生物。基于这一发现，在[18 F]氟化物的干燥过程中避免乙腈以及18 F标记使得能够制备仅含有少量相应醇的18 F标记化合物。最后，我们使用自动合成仪实现了18F标记的芪衍生物作为18F标记的淀粉样蛋白β配体的高效相位标签辅助合成。
We found that acetonitrile acted as a reactant under the conventional reaction conditions for aliphatic nucleophilic18F‐fluorination in acetonitrile to provide theN‐alkyl 3‐aminobut‐2‐enenitrile as one of the side products. Dimerization of acetonitrile promoted by a complex of K2CO3and K222 provided 3‐aminobut‐2‐enenitrile, which acted as nucleophile to provideN‐alkyl amino derivatives. Based on the finding, avoiding acetonitrile in the drying of [18F]fluoride as well as18F‐labeling enabled the preparation of18F‐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 of18F‐labeled stilbene derivative as a18F‐labeled amyloid‐β ligand.