Recycling the tert-butanesulfinyl group in the synthesis of amines using tert-butanesulfinamide

M Wakayama, JA Ellman

Index: Wakayama, Masakazu; Ellman, Jonathan A. Journal of Organic Chemistry, 2009 , vol. 74, # 7 p. 2646 - 2650

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Citation Number: 53

Abstract

A practical process for recycling the tert-butanesulfinyl group upon deprotection of N-tert- butanesulfinyl amines has been achieved. Treatment of N-tert-butanesulfinyl amines with HCl in cyclopentyl methyl ether results in complete conversion to tert-butanesulfinyl chloride and the corresponding amine hydrochloride salt, which is isolated by filtration in analytically pure form and in quantitative yield. Treatment of the resulting sulfinyl chloride solution with ...