Tetrahedron letters

One-pot conversion of azides to Boc-protected amines with trimethylphosphine and Boc-ON

X Ariza, F Urpí, C Viladomat, J Vilarrasa

Index: Ariza, Xavier; Urpi, Felix; Viladomat, Carles; Vilarrasa, Jaume Tetrahedron Letters, 1998 ,  vol. 39,  # 49  p. 9101 - 9102

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Citation Number: 65

Abstract

Reaction of azides with trimethylphosphine followed by addition of 2-(tert- butoxycarbonyloxyimino)-2-phenyl-acetonitrile (Boc-ON) at− 20° C and stirring at rt for 5 h affords the desired Boc-amines in 87–100% yields. Similar yields are obtained by mixing all components together (azide, Me3P, and Boc-ON) in toluene or THF.