Synthesis of four racemic nicotine isotopomers doubly labelled with stable isotope |
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Authors: | Wilfried Hatton Virginie Silvestre Richard J. Robins Monique Mathé‐Allainmat Jacques Lebreton |
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Affiliation: | Université de Nantes, CNRS, Laboratoire de Chimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR‐CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France |
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Abstract: | Four racemic nicotine isotopomers, doubly labelled with stable isotope, were prepared for use in studies of plant metabolism. First, starting from halogeno nicotinates, one deuterium was introduced into the pyridine moiety by reductive dehalogenation with zinc, and choosing deuterated acetic acid as the acidic medium. Pyridine 2H‐labelled nornicotine derivatives were then formed in two reaction steps, a condensation reaction with N‐vinylpyrrolidinone followed by catalytic hydrogenation. The deuteromethylation of these monodeuterated nornicotines was achieved by reduction of the corresponding ethyl carbamates with deuterated lithium aluminium hydride. The four regioisotopomers obtained were at the least 90% labelled on each site, sufficient for the metabolic studies envisaged. Copyright © 2009 John Wiley & Sons, Ltd. |
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Keywords: | deuterated pyridine N‐2H‐methylation 2H‐labelled compounds nicotine |
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