Evaluation of several routes to advanced pregabalin intermediates: Synthesis and enantioselective enzymatic reduction using ene-reductases

S Debarge, P McDaid, P O'Neill, J Frahill…

文献索引：Winkler, Christoph K.; Clay, Dorina; Davies, Simon; O'Neill, Pat; McDaid, Paul; Debarge, Sebastien; Steflik, Jeremy; Karmilowicz, Mike; Wong, John W.; Faber, Kurt Journal of Organic Chemistry, 2013 , vol. 78, # 4 p. 1525 - 1533

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被引用次数: 13

摘要

This publication describes the evaluation of four synthetic routes to the advanced pregabalin (Lyrica) intermediate 7. Asymmetric reduction of (E)-7 with an ene-reductase (OPR1 from Lycopersicon esculentum) gave a saturated cyanoester intermediate 5 with the desired S stereocenter in> 99% ee. OPR1 also catalyzed the reduction of (Z)-7 to (S)-5, but with lower conversion and selectivity.