MONO-PROTECTED DIAMINES - N-TERT-BUTOXYCARBONYL-ALPHA,OMEGA-ALKANEDIAMINES FROM ALPHA,OMEGA-ALKANEDIAMINES

We wish to report a convenient pathway to N-tert-butoxycarbonyI-α,ω- alkanediamines 2a-e [H2N(CH2)xNHBOC; x= 2, 3, 4, 5 and 6; (75-90% yields)] by treatment of the corresponding α,ω-alkanediamine with di-tert-butyl dicarbonate in dioxane as the solvent. Only small amounts of the bis-substituted N,N'-tert-butoxycarbonyl-α,ω-alkanediamines 3a-e were formed (2-9%) which were easily removed by an aqueous workup. The α,ω-alkane-aza-diamine 4 was also mono-protected (62% yield of 5) by the same methodology. © 1990, Taylor & Francis Group, LLC. All rights reserved.