Direct fixation of [11C]-CO2 by amines: formation of [11C-carbonyl]-methylcarbamates

Alan A. Wilson; Armando Garcia; Sylvain Houle; Neil Vasdev

doi:10.1039/B916419G

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Organic & Biomolecular Chemistry

Issue 2, 2010

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Direct fixation of [¹¹C]-CO₂ by amines: formation of [¹¹C-carbonyl]-methylcarbamates

Alan A. Wilson , Armando Garcia , Sylvain Houle and Neil Vasdev

Org. Biomol. Chem., 2010, 8, 428-432

DOI: 10.1039/B916419G
Received 11 Aug 2009, Accepted 05 Oct 2009
First published on the web 18 Nov 2009

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Abstract
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[¹¹C-Carbonyl]-methylcarbamates can be synthesised directly from [¹¹C]-CO₂ and primary or secondary amines in a one-pot, two-step reaction. The use of either diazabicyclo[5.4.0]undec-7-ene (DBU) or 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) enables efficient trapping of [¹¹C]-CO₂ in small volumes of DMF as [¹¹C]-carbamate salts. Subsequent reaction with a variety of methylating agents rapidly generates the desired [¹¹C-carbonyl]-methylcarbamates in high radiochemical yields. The usefulness of the method is illustrated by the efficient radiosynthesis of a kappa opioid receptor imaging radiotracer, useful in positron emission tomography (PET).

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Supplementary Info

Full experimental details on the radiosynthesis of [ ¹¹C- carbonyl]-GR103545, [ ¹¹C]-CO ₂ gas–liquid partition data, and ¹H and ¹³C NMR spectra of 4-(2-methoxyphenyl)-1-piperazinecarboxylic acid methyl ester
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Organic & Biomolecular Chemistry

Direct fixation of [¹¹C]-CO₂ by amines: formation of [¹¹C-carbonyl]-methylcarbamates

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