[18F]Fluoroamines via ring-opening of N-Cbz-2-methylaziridine with [18F]-fluoride

A highly regioselective method was developed for ring-opening benzyloxycarbonyl (Cbz)-protected 2-methylaziridine with [18F]-labelled fluoride. Following catalytic hydrogenation, 1-[18F]fluoro-2-propanamine ([18F]1) and 2-[18F]fluoro-1-propanamine ([18F]2) were prepared as the major and minor products, respectively (85:15), and were characterized following acylation with benzyl chloride. This methodology is applicable towards the generation of new [18F]-labelled amines for incorporation into radiopharmaceuticals.

Synthetically versatile [18F]-labelled amines were prepared by ring-opening of an activated unsymmetrical aziridine with [18F]-fluoride, followed by deprotection.Figure optionsDownload as PowerPoint slide