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Synthesis 2010(21): 3596-3601  
DOI: 10.1055/s-0030-1258295
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© Georg Thieme Verlag Stuttgart ˙ New York

Practical Synthesis of Optically Pure Menthylamines Starting from Racemic Neomenthol

Nina Welschoffa, Siegfried R. Waldvogel*a,b
a Kekulé Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
b Institute for Organic Chemistry, Johannes-Gutenberg University Mainz, Duesberg 10-24, 55128 Mainz, Germany
Fax: +49(6131)3926777; e-Mail: waldvogel@uni-mainz.de;
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Publication History

Received 20 August 2010
Publication Date:
13 October 2010 (online)

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Abstract

A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.

Key words

amines - azides - chiral resolution - reduction - terpenoids

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