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Synthesis of a 13C labeled N-cyclopropylamine tetrahydropyridine derivative

✍ Scribed by Simon Kuttab; Stephan Mabic

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
108 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of 1‐(2‐^13^C)‐cyclopropyl‐4‐phenyl‐1,2,3,6‐tetrahydropyridine (8) is reported. Attempts were first made to prepare labeled cyclopropylamine via a cyclopropanation/Curtius rearrangement sequence, but the yields were too modest to be suitable for the synthesis of a labeled compound. The preparation of 8 was achieved via cyclopropanation of the N‐formyl tetrahydropyridine derivative 21 using the Grignard reagent of ethyl bromide and Ti(O‐__i__Pr)~4~ as a catalyst. The synthesis proceeded in high yield (82%). The method has a wide potential for the synthesis of other cyclopropyl ring labeled and substituted cyclopropyl ring labeled tetrahydropyridine dervatives which can be used in Monoamine Oxidase (MAO) and Cyt P~450~ enzymes mechanistic studies. Copyright © 2002 John Wiley & Sons, Ltd.

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