Selective Nosylation of 1-Phenylpropane-1,3-diol and Perchloric Acid Mediated Friedel-Crafts Alkylation: Key Steps for the New and Straightforward Synthesis of Tolterodine

Kathlia A. De Castro; Hakjune Rhee

doi:10.1055/s-2008-1067084

PAPER

Selective Nosylation of 1-Phenylpropane-1,3-diol and Perchloric Acid Mediated Friedel-Crafts Alkylation: Key Steps for the New and Straightforward Synthesis of Tolterodine

Kathlia A. De Castro, Hakjune Rhee*
Department of Chemistry and Applied Chemistry, Hanyang University, Ansan Sa-3-Dong 1271, Kyunggi-Do 426-791, Korea
Fax: +82(31)4073863; e-Mail: hrhee@hanyang.ac.kr;

Abstract

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Abstract

We have developed a new and straightforward synthesis of racemic tolterodine [N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine]. The synthesis involves selective nosylation on the primary alcohol of 1-phenylpropane-1,3-diol using 4-nitrobenzenesulfonyl chloride, subsequent diisopropylamine substitution, and Friedel-Crafts alkylation using aqueous perchloric acid.

Key words

drugs - diol - selective sulfonation - nucleophilic substitution - Friedel-Crafts alkylation

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