Enantioselective formal synthesis of pregabalin with bifunctional acid/base organocatalysts

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2013

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Kapucu, Merve

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Pregabalin, which is marketed under the brand name of Lyrica by Pfizer, is an important chiral drug in the treatment of epilepsy and neuropathic pain. Since only S-Pregabalin is active for the treatment, asymmetric synthesis was accomplished in 6 steps and the chiral induction was done by transition metal catalysis in industrial production. In this thesis, we applied an alternative synthetic route taken place in 3 steps. The key step comprised the chiral induction done by organocatalysis and the formal asymmetric synthesis of Pregabalin has been performed by Michael type addition of diethyl malonate to (E)-4-Methyl-1-nitro-1-pentene in 81% ee. Parallel to this work, different Michael acceptors and donors were used to test our catalyts’ activities.

Subject Keywords

Pregabalin., Catalysis., Asymmetric synthesis., Enantioselective catalysis.

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http://etd.lib.metu.edu.tr/upload/12616702/index.pdf
https://hdl.handle.net/11511/23215

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

M. Kapucu, “Enantioselective formal synthesis of pregabalin with bifunctional acid/base organocatalysts,” M.S. - Master of Science, Middle East Technical University, 2013.