Synthesis and application of isocyanates radiolabeled with carbon-11

Abstract

Carbon-11 labeled isocyanates are efficiently prepared by dehydration of [(11) C]carbamate salts, which in turn are easily formed from cyclotron-produced [(11) C]CO(2) and amines in the presence of a CO(2) fixation agent. The [(11) C]isocyanates are useful radiosynthons for the synthesis of a variety of [carbonyl-(11) C]-labeled asymmetrical ureas and carbamate esters. The method is well suited to incorporate any isotope of carbon, and is especially useful for positron emission tomography (PET) radiotracers for in vivo imaging. This is demonstrated by using the method to make [carbonyl-(11) C]-6-hydroxy-[1,1'-biphenyl]-3-yl cyclohexylcarbamate which is a novel radiotracer for PET imaging of fatty acid amide hydrolase.