Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine

Olexiy S. Artamonov; Evgeniy Y. Slobodyanyuk; Oleg V. Shishkin; Igor V. Komarov; Pavel K. Mykhailiuk

doi:10.1055/s-0032-1316831

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(2): 225-230
DOI: 10.1055/s-0032-1316831

paper

Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine

Authors

Olexiy S. Artamonov

^aInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv-94 02660, Ukraine
Evgeniy Y. Slobodyanyuk

^bEnamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine eMail: Pavel.Mykhailiuk@gmail.com

^cDepartment of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
Oleg V. Shishkin

^dSTC, ‘Institute for Single Crystals,’ National Academy of Science, 60 Lenina ave., Kharkiv 61001, Ukraine
Igor V. Komarov

^bEnamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine eMail: Pavel.Mykhailiuk@gmail.com

^cDepartment of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
Pavel K. Mykhailiuk*

^bEnamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine eMail: Pavel.Mykhailiuk@gmail.com

^cDepartment of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine

Abstract

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Abstract

Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.

Key words

amines - trifluoromethyl group - cyclopropane - 4-trifluoromethylpiperidine - drug design

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Referenzen

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Zusatzmaterial

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