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Synthesis 2011(1): 119-122  
DOI: 10.1055/s-0030-1258323
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Multigram Synthesis of trans-2-(Trifluoromethyl)cyclopropanamine

Andrii V. Bezdudnya,b, Denis Klukovskya,b, Natalia Simurovab, Pavel K. Mykhailiuk*a,c, Oleg V. Shishkind, Yurii M. Pustovita,b
a Enamine Ltd., Oleksandra Matrosova Street 23, 01103 Kyiv, Ukraine
Fax: +380(44)2351273; e-Mail: Pavel.Mykhailiuk@gmail.com;
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, 02660 Kyiv-94, Ukraine
c Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, 01033 Kyiv, Ukraine
d STC, Institute for Single Crystals, National Academy of Science of Ukraine, 60 Lenina Avenue, 61001 Kharkiv, Ukraine
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Publikationsverlauf

Received 24 September 2010
Publikationsdatum:
12. November 2010 (online)

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Abstract

2-(Trifluoromethyl)cyclopropanamine was synthesized. The key step of the synthesis is a transformation of the carboxy group into the trifluoromethyl group by using sulfur tetrafluoride. Twenty gram of the target product was conveniently prepared in a single batch.

Key words

fluorine - trifluoromethyl group - amines - cyclopropyl group - sulfur tetrafluoride

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4

A DiscoveryGate search in August 2010 revealed that 57728 N-substituted derivatives of cyclopropanamine are commercially available.

7

Compound 2 is mentioned in Ref. 6a; however, neither the preparation procedure nor the analytical or NMR data are given.