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Synthesis of a 13 C labeled N ‐cyclopropylamine tetrahydropyridine derivative
Author(s) -
Kuttab Simon,
Mabic Stephan
Publication year - 2002
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.605
Subject(s) - chemistry , cyclopropanation , curtius rearrangement , bromide , derivative (finance) , yield (engineering) , stereochemistry , ring (chemistry) , chemical synthesis , catalysis , organic chemistry , metallurgy , biochemistry , materials science , financial economics , economics , in vitro
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.