Synthesis of 2,6-diazabicyclo[3.3.1]nonanes via intramolecular cycloaddition of nitrones
Ryosuke Kawai1, Asano Nakamura1, Yui Irie1
1Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya 464-8601, Japan. yokoshima.satoshi.v7@f.mail.nagoya-u.ac.jp.
Abstract:
A new synthesis route to 2,6-diazabicyclo[3.3.1]nonanes as a scaffold of conformationally restricted diamines is disclosed. Starting from 4-amino-1-Boc-piperidine (Boc = tert-butoxycarbonyl), introduction of an alkene unit on the 4-amino group, followed by removal of the Boc group, afforded secondary amines. Subsequent oxidation of the amines with Oxone furnished nitrones, which underwent intramolecular cycloaddition to construct the 2,6-diazabicyclo[3.3.1]nonane skeleton.
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