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An efficient and convergent synthesis of the potent and selective H3 antagonist ABT-239
- Source :
-
Tetrahedron . May2006, Vol. 62 Issue 18, p4584-4589. 6p. - Publication Year :
- 2006
-
Abstract
- Abstract: An efficient and convergent process for the preparation of a potent and selective H3 receptor antagonist, ABT-239, 1A was accomplished with an overall yield of 64%. The key step in the synthesis is a Sonogashira coupling/cyclization reaction of 1-but-3-ynyl-2-(R)-methylpyrrolidine ( 9 ) with 4′-hydroxy-3′-iodo-biphenyl-4-carbonitrile ( 3 ). Additionally, the key amine component 2-(R)-methylpyrrolidine ( 7 ) was effectively synthesized from the readily available Boc-l-prolinol with a simple catalytical hydrogenolysis as the key step. This column chromatography-free process is highlighted by several simple work-up and purification procedures and is amendable to the large-scale preparation of 1A . [Copyright &y& Elsevier]
- Subjects :
- *ORGANIC compounds
*CHROMATOGRAPHIC analysis
*HYDROLYSIS
*HYDROGENATION
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 62
- Issue :
- 18
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 20551125
- Full Text :
- https://doi.org/10.1016/j.tet.2006.02.046