Chesis P L, Welch M J
Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, MO 63110.
Int J Rad Appl Instrum A. 1990;41(3):259-65. doi: 10.1016/0883-2889(90)90189-n.
The use of 3-bromopropyl-1-trifluoromethanesulfonate and 3-iodopropyl-1-trifluoromethanesulfonate (triflates) as precursors for 18F-labeling of a secondary amine is described. This simple two step procedure, [18F]fluoride triflate displacement followed by N-alkylation, has been optimized using N-nordiprenorphine as the model substrate. The highest radiochemical yields (85%) for the triflate displacement reaction were obtained in THF using n-Bu4 NOH as the base. In comparing the two triflates no differences in the yields for this step were observed. In contrast, the yields for the fluoroalkylation step were increased more than 75% by using 1-[18F]fluoro-3-iodopropane rather than 1-bromo-3-[18F]fluoropropane. The highest yields for this N-alkylation reaction (35%) were achieved in DMF using N,N-diisopropylethylamine as the base. For both steps the observed yields are strongly dependent on the relative concentrations of the major reactants.
描述了使用3-溴丙基-1-三氟甲磺酸酯和3-碘丙基-1-三氟甲磺酸酯（三氟甲磺酸酯）作为仲胺18F标记前体的方法。以N-去甲二氢吗啡酮作为模型底物，对这个简单的两步程序进行了优化，即[18F]氟化物三氟甲磺酸酯取代反应，然后进行N-烷基化反应。在四氢呋喃中使用氢氧化四丁铵作为碱，三氟甲磺酸酯取代反应获得了最高的放射化学产率（85%）。比较这两种三氟甲磺酸酯时，未观察到该步骤产率的差异。相比之下，通过使用1-[18F]氟-3-碘丙烷而非1-溴-3-[18F]氟丙烷，氟烷基化步骤的产率提高了75%以上。在N,N-二异丙基乙胺作为碱的情况下，在N,N-二甲基甲酰胺中实现了该N-烷基化反应的最高产率（35%）。对于这两个步骤，观察到的产率在很大程度上取决于主要反应物的相对浓度。
