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Nucleophilic substitutions using O-alkyl-N,N′-dialkylisoureas. Applications to ephedrines

✍ Scribed by Martin A. Poelert; Richard M. Kellogg; L. A. Hulshof

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
527 KB
Volume
113
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Dialkylcarbodiimides in the presence of a Cu^1^ catalyst react cleanly with the hydroxyl group of N‐methylated (1__R__,2__S__)‐ephedrine and (1__S__,2__S__)‐pseudoephedrine. These adducts react with nucleophiles like alkyl and aryl thiols as well as thioic acids and phthalimide to form the substitution products with overall retention of configuration. It is postulated that intramolecular participation of the amino group via an S~N~2 reaction leads to aziridium salts, which are subsequently opened by the nucleophiles via a second S~N~2 reaction. This synthetic approach is also useful for the inversion of simple secondary alcohols; on treatment with dicyclohexylcarbodiimide followed by benzothioic acid and treatment with LiAlH~4~, menthol was converted in good yield to neomenthane thiol.

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