Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor

Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor

An enantioselective Overman 3,3-sigmatropic rearrangement on a quinuclidine skeleton was developed for the pilot-plant synthesis of a glycine transporter 1 inhibitor. The first stereocenter was produced by a Ru-catalyzed asymmetric transfer hydrogenation process followed by chirality transfer using...

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Veröffentlicht in:Organic process research & development 2012-03, Vol.16 (3), p.484-494
Hauptverfasser: Chandramouli, Sithamalli V, Ayers, Timothy A, Wu, Xiao-Dong, Tran, Loc T, Peers, James H, Disanto, Rocco, Roberts, Frederick, Kumar, Narendra, Jiang, Ying, Choy, Nakyen, Pemberton, Clive, Powers, Matthew R, Gardetto, Anthony J, D’Netto, Geoffrey A, Chen, Xuemin, Gamboa, Juan, Ngo, Duc, Copeland, Warren, Rudisill, Duane E, Bridge, Andrew W, Vanasse, Benoit J, Lythgoe, David J
Format: Artikel
Sprache:eng
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Zusammenfassung:An enantioselective Overman 3,3-sigmatropic rearrangement on a quinuclidine skeleton was developed for the pilot-plant synthesis of a glycine transporter 1 inhibitor. The first stereocenter was produced by a Ru-catalyzed asymmetric transfer hydrogenation process followed by chirality transfer using the Overman rearrangement. The second stereocenter was generated by a diastereoselective hydrogenation reaction.
ISSN:1083-6160
1520-586X
DOI:10.1021/op200378r