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Synthesis 2012(8): 1152-1154  
DOI: 10.1055/s-0031-1289711
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Safe Method for the Multigram Synthesis of trans-2-(Trifluoromethyl)cyclopropylamine

Vladimir S. Yarmolchuka,b, Andrii V. Bezdudnya, Nataliya A. Tolmachevaa, Oleg Lukin*c, Alexander N. Boykoc, Alexey Chekotyloc, Andrei A. Tolmacheva,c, Pavel K. Mykhailiuk*a,b
a Enamine Ltd., Alexander Matrosov St. 23, Kiev 01103, Ukraine
e-Mail: pavel.mykhailiuk@gmail.com;
b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska St. 64, Kiev 01033, Ukraine
c ChemBioCenter, Kiev National Taras Shevchenko University, Volodymyrska St. 62, Kiev 01033, Ukraine
Fax: +38(44)2351273; e-Mail: oleg.lukin@univ.kiev.ua;
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Publikationsverlauf

Received 28 November 2011
Publikationsdatum:
15. Februar 2012 (online)

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Abstract

trans-2-(Trifluoromethyl)cyclopropylamine was prepared on a multigram scale from readily accessible 4,4,4-trifluorobut-2-enoic acid in five steps. The key step was a high-yielding cyclopropane ring formation from 4,4,4-trifluorobut-2-enoic acid methoxymethyl amide under Corey-Chaykovsky reaction conditions.

Key words

cyclopropyl group - amines - trifluoromethyl group - fluorine - Corey-Chaykovsky cyclopropanation

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5

For the list of occupational exposure limits for SF4, see the Advisory reports from the Health Council of The Netherlands at http://www.gezondheidsraad.nl/en/publications.