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Chiral pregabalin synthesis

The first enantioselective synthesis of pregabalin (2) was developed by Yuen and co-workers at Pfizer using Evans chiral oxazolidinone chemistry (Yuen et al., 1994). [Pg.234]

Many of the synthetic routes derived for pregabalin (2) before 2003 have relied on classical chiral resolution of either an intermediate or the final racemic 3-isobutyl GABA (43). In 2003, Jacobsen and co-workers published their work on a novel enantio-selective synthesis of pregabalin (2) (Sammis and Jacobsen, 2003). The Harvard group was able to promote conjugate addition of hydrogen cyanide into the unsaturated imide... [Pg.236]

Kissel, Ramsden, and other researchers at Pfizer and Chirotech jointly published a novel chiral synthesis of pregabalin (2) in 2003 based on asymmetric hydrogenation (Burk et al., 2001, 2003). Their synthesis started with the condensation of isobutyralde-hyde with acrylonitrile under Baylis-Hillman conditions to give allylic alcohol 65. This alcohol was activated as the carbonate 66 and subjected to palladium-catalyzed car-bonylation conditions to give cyanoester 67. The ester 67 was hydrolyzed and converted to... [Pg.237]

Scheme 8.1 Initial synthesis of pregabalin in its chiral form. Scheme 8.1 Initial synthesis of pregabalin in its chiral form.
Selective reductien toward chiral a-bromoe ters 58 for type 2 diabetes API 60 functionalization using OYEs (top) [94] synthesis of various (/Q-Profen derivatives 63 using YqjM (centei) [107] application of 11 EREDs in the preparation of ( -Pregabalin 66 and other 7-aminobutyric add (bottom) analogs [108]. [Pg.260]


See other pages where Chiral pregabalin synthesis is mentioned: [Pg.783]    [Pg.69]    [Pg.336]    [Pg.1370]    [Pg.51]    [Pg.1370]   
See also in sourсe #XX -- [ Pg.161 , Pg.162 ]




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