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Synthesis 2008(14): 2298-2302  
DOI: 10.1055/s-2008-1067156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel and Facile One-Pot Method for the Synthesis of N-Substituted Sulfamates

Hallena Rogers*, Guy Humphrey, Anna Chiu, Tao Pei
Department of Process Research, Merck and Co Inc., 126 E. Lincoln Avenue, P.O. Box 2000, Rahway, NJ 07065, USA
Fax: +1(732)5941499; e-Mail: hallena_rogers@merck.com;
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Publication History

Received 14 April 2008
Publication Date:
02 July 2008 (online)

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Abstract

A one-pot approach to the formation of N-substituted sulfamates from carboxylic acids using di-tert-butyl dicarbonate, tetrabutylammonium sulfamate, and pyridine under mild conditions is described. A reaction mechanism with two competing pathways is proposed; in reactions with aliphatic and electron-deficient aromatic acid substrates, the desired sulfamate products are formed, in contrast, symmetrical anhydride intermediates are observed with electron-neutral or electron-rich aromatic substrates.

Key words

sulfamates - carboxylic acid - tetrabutylammonium sulfamate - carbonate - anhydride