Ring opening of N-tosylhistamine with di-t-butyl pyrocarbonate: synthesis of 1,2-diamino-4-tosylaminobutane dihydrochloride

Abstract

Bamberger ring-cleavage acylation of N-tosylhistamine with di-t-butyl pyrocarbonate [Bu^tOC(:O)–O–C(:O)OBu^t] in acetonitrile–aqueous potassium acetate leads to 3,4-bis(di-t-butoxycarbonylamino)but-3-enyl(tosyl)amine, which, after hydrogenation and treatment with hydrochloric acid, gives 1,2-diamino-4-tosylaminobutane dihyrochloride.