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Synfacts 2010(12): 1328-1328
DOI: 10.1055/s-0030-1258867
DOI: 10.1055/s-0030-1258867
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (S)-(-)-Ropivacaine
T. K. Beng, R. E. Gawley*
University of Arkansas, Fayetteville, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2010 (online)

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.