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Synfacts 2010(12): 1328-1328  
DOI: 10.1055/s-0030-1258867
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (S)-(-)-Ropivacaine

Contributor(s): Philip Kocienski
T. K. Beng, R. E. Gawley*
University of Arkansas, Fayetteville, USA
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

rac-2-Lithio-N-Boc-piperidine (B) undergoes catalytic dynamic resolution on treatment with TMEDA and 0.1 equivalent of the chiral ligand (S,R)-C at -78 ˚C. The resultant α-lithiated piperidine D was quenched with isocyanate E to afford the amide F with an er of >99:1. Amide F was converted into (S)-(-)-ropivacaine, a local ­anesthetic marketed by AstraZeneca. The enantiomeric series can be easily accessed with equal efficiency by using the chiral ligand (S,S)-C.