A practical synthesis of (1S, 4S)-2, 5-diazabicyclo [2.2. 1] heptane

C Beinat, SD Banister, CSP McErlean, M Kassiou

Index: Beinat, Corinne; Banister, Samuel D.; McErlean, Christopher S.P.; Kassiou, Michael Tetrahedron Letters, 2013 , vol. 54, # 39 p. 5345 - 5347

Full Text: HTML

Citation Number: 6

Abstract

Abstract The rigid piperazine homologue 2, 5-diazabicyclo [2.2. 1] heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation