An improved and scalable process for 3,8-diazabicyclo[3.2.1] octane analogues

An improved and scalable process for substituted 3,8-diazabicyclo[3.2.1]octane was developed. N-Benzyl-2,5-dicarbethoxypyrrolidine 2 was reduced to N-benzyl-2,5-dihydroxymethylpyrrolidine 9 and subsequently debenzylated to afford N-Boc-2,5-dihydroxymethylpyrrolidine 10. After mesylation of the diol 10 and cyclization with benzylamine, a diversity of scaffold, 3,8-diazabicyclo[3.2.1]octane analogue 12 was obtained in a total yield of 42% in five steps. (c) 2010 Da Wei Teng. Published by Elsevier B.V, on behalf of Chinese Chemical Society. All rights reserved.