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Synthesis 2010(3): 443-446  
DOI: 10.1055/s-0029-1217141
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Simple and Efficient Procedure for a Multigram Synthesis of Both trans- and cis-1-Amino-2-(trifluoromethyl)cyclopropane-1-carboxylic Acid

Olexiy S. Artamonova,b, Pavel K. Mykhailiuk*a,b, Nataliia M. Voievodaa,b, Dmitry M. Volochnyukb,c, Igor V. Komarova,b
a Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska St. 64, 01033 Kyiv, Ukraine
b Enamine Ltd., Oleksandra Matrosova St. 23, 01103 Kyiv, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska St. 5, 02660 Kyiv-94, Ukraine
Fax: +380(44)2351273; e-Mail: pashamk@gmx.de;
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Publication History

Received 30 September 2009
Publication Date:
20 November 2009 (online)

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Abstract

A simple and efficient procedure for the multigram synthesis of both (±)-trans- and (±)-cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid was developed. The key step of the synthesis is the addition of 1-diazo-2,2,2-trifluoroethane to methyl 2-[(tert-butoxycarbonyl)amino]acrylate, followed by thermal decomposition of the resulting pyrazoline. Gram quantities of trans- and cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid were easily prepared from l-serine in one synthetic run.

Key words

fluorine - alkenes - amino acids - catalysts - diazo compounds

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10

The ¹H NMR spectrum of the isomer 8b is identical to that described in ref. 7b (see the experimental section).