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Synthesis 2010(23): 3967-3973  
DOI: 10.1055/s-0030-1258964
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Productive Syntheses of 1-Ethynylcyclopropylamine and 1-Ethynylcyclobutylamine [¹]

Sergei I. Kozhushkova, Karsten Wagner-Gillena, Alexander F. Khlebnikovb, Armin de Meijere*a
a Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany
Fax: +49(551)23422; e-Mail: ameijer1@uni-goettingen.de;
b Department of Chemistry, Saint Petersburg State University, Universitetskii Prosp. 26, Petrodvorets, 198504 St. Petersburg, Russian Federation
Further Information

Publication History

Received 3 September 2010
Publication Date:
09 November 2010 (online)

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Abstract

The new 1,1-dimethylpropargylamine surrogates, 1-ethynylcyclopropylamine (3) and 1-ethynylcyclobutylamine (5), were prepared as hydrochlorides from cyclopropylacetylene and 6-chlorohex-1-yne in overall yields of 39 and 25%, respectively, on a scale of up to 300 mmol. The amine 3 was converted into the new ethynyl-extended 1-aminocyclopropanecarboxylic acid 4, and both the amine 3 as well as the amino acid 4 were made available as their N-Fmoc-protected derivatives.

Key words

alkynes - amines - amino acids - Curtius degradation - small rings

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17

For an alternative synthesis of 7 from trimethylsilyl-acetylene, see ref. 15b.

24

Cabrele, C.; Kozhushkov, S. I.; de Meijere, A., unpublished results.