N-Boc 4-nitropiperidine: preparation and conversion into a spiropiperidine analogue of the eastern part of maraviroc

A simple preparation of previously unreported N-Boc 4-nitropiperidine is described. The synthetic utility of this new intermediate is illustrated by the synthesis of a spiropiperidine analogue of the eastern part of maraviroc. Previously unreported N-Boc 4-nitropiperidine was prepared in two steps f...

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Bibliographic Details
Published in:Tetrahedron letters 2010-06, Vol.51 (24), p.3216-3217
Main Authors: Mullen, Philip, Miel, Hugues, Anthony McKervey, M.
Format: Article
Language:English
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Summary:A simple preparation of previously unreported N-Boc 4-nitropiperidine is described. The synthetic utility of this new intermediate is illustrated by the synthesis of a spiropiperidine analogue of the eastern part of maraviroc. Previously unreported N-Boc 4-nitropiperidine was prepared in two steps from N-Boc-piperidone. The synthetic utility of this new intermediate was demonstrated by the development of a new and simple route to spirolactam piperidines. Further synthetic work involving a challenging triazole cyclisation allowed the preparation of a spiropiperidine analogue of the eastern part of maraviroc.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.04.046