Author(s)

Chunying Wu, Ruoshi Li, Dorr Dearborn, Yanming Wang

Division of Radiopharmaceutical Science, Case Center for Imaging Research, Department of Radiology, Cleveland, USA.
Environmental Health, Case Western Reserve University, Cleveland, USA.

Carbon-11 radiolabeled amines constitute a very important class of radioligands that are widely used for positron emission tomography (PET) imaging. Radiolabeling of amines is often achieved through radiomethylation using [¹¹C]CH₃I or [¹¹C]CH₃OTf under basic conditions in a strictly anhydrous environment. Functional groups such as hydroxyl and carboxyl groups that are often present in the molecules are normally base sensitive and require protection and deprotection, which substantially prolongs and complicates the radiolabeling process. Here we report a versatile approach to a series of C-11 radiolabeled amines prepared through reductive amination using [¹¹C]formaldehyde. Using a variety of substrates bearing different functional groups, we demonstrate the general utility of this method. In contrast to conventional radiomethylation methods, the reductive amination using [¹¹C]formaldehyde can be carried out in an aqueous environment relatively quickly without the need of protection of base-sensitive functional groups.

C-11 Formaldehyde; Radiomethylation; Reductive Amination; Positron Emission Tomography; Radiolabelling

Wu, C. , Li, R. , Dearborn, D. and Wang, Y. (2012) Reductive Amination with [¹¹C]Formaldehyde: A Versatile Approach to Radiomethylation of Amines. International Journal of Organic Chemistry, 2, 202-223. doi: 10.4236/ijoc.2012.23030.