Journal
TETRAHEDRON LETTERS
Volume 54, Issue 37, Pages 5096-5098Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.07.042
Keywords
CP-690,550; JAK3 inhibitor; Mitsunobu reaction; Alane reduction
Categories
Funding
- Fondecyt [1110022]
- Anillo ACT [11107]
- CONICYT 'Programa Atraccion e Insercion de Capital Humano Avanzado' [79090038]
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A novel stereoselective synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor, has been achieved starting from (5S)-5-hydroxypiperidin-2-one in 10 steps from 2 with a 9.5% overall yield. The potentiality of this synthetic route is the obtention of tert-butyl-(3S,4R)-3-hydroxy-4-methylpiperidine-1-carboxylate (6b) as a new chiral precursor involved in the synthesis of CP690,550, in a three-step reaction, without epimerizations, rather than the 5 or more steps used in described reactions to achieve this compound from analogues of 6b. (C) 2013 Elsevier Ltd. All rights reserved.
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