A New, Simple Synthesis of N-Tosyl Pyrrolidines and Piperidines

Maria Carla Marcotullio; Valerio Campagna; Silvia Sternativo; Ferdinando Costantino; Massimo Curini

doi:10.1055/s-2006-942488

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Synthesis 2006(16): 2760-2766
DOI: 10.1055/s-2006-942488

PAPER

A New, Simple Synthesis of N-Tosyl Pyrrolidines and Piperidines

Maria Carla Marcotullio*^a, Valerio Campagna^a, Silvia Sternativo^a, Ferdinando Costantino^b, Massimo Curini^a
^a Dipartimento di Chimica e Tecnologia del Farmaco, Sez, Chimica Organica-Università degli Studi, 06123 Perugia, Italy
Fax: +39(075)5855116; e-Mail: marcotu@unipg.it;
^b Dipartimento di Chimica-Università degli Studi, 06123 Perugia, Italy

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Publication History

Received 25 January 2006
Publication Date:
12 July 2006 (online)

Abstract
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Abstract

Iodocyclization of unsaturated tosylamides promoted by Oxone^® oxidation of KI afforded, in good yields, N-tosyl iodopyrrolidines and piperidines. A new, simple method for the conversion of alcohols to tosylamides is presented.

Key words

pyrrolidines - piperidines - Oxone^® - iodocyclization - toluenesulfonamides

References

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Compound 3 showed [α]_D ²⁴ +4.06 (c 2.15, CH₂Cl₂). This value is comparable with the [α] value of the same tosylamide prepared from commercial (R)-2-octyl amine by reaction with p-toluenesulfonyl chloride {[α]_D ²³ +5.0 (c 1.7, CH₂Cl₂)}.

11

CCDC reference number 292928.