Tetrahedron Letters

A convenient route to 1-benzyl 3-aminopyrrolidine and 3-aminopiperidine

L Jean, I Baglin, J Rouden, J Maddaluno, MC Lasne

Index: Jean, Ludovic; Baglin, Isabelle; Rouden, Jacques; Maddaluno, Jacques; Lasne, Marie-Claire Tetrahedron Letters, 2001 , vol. 42, # 33 p. 5645 - 5649

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Citation Number: 25

Abstract

1-Benzyl 3-aminopyrrolidine 1 and 1-benzyl 3-aminopiperidine 2 were prepared rapidly mainly in aqueous conditions in 55 and 75% yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The key step involved the Curtius rearrangement mediated by sodium nitrite and trifluoroacetic acid of the appropriate acylhydrazides. All the reactions (except LAH reductions) were performed in ...