Racemisation of R-bupivacaine: a key factor in the integrated and economic process for the production of levobupivacaine

…, G Hutton, CJ Lock, BM Skead, M Woods…

Index: Langston, Marianne; Dyer, Ulrich C.; Frampton, Graham A.C.; Hutton, Gordon; Lock, Christopher J.; Skead, Benjamin M.; Woods, Martin; Zavareh, Hooshang S. Organic Process Research and Development, 2000 , vol. 4, # 6 p. 530 - 533

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Citation Number: 13

Abstract

Two methods for the racemisation of nonracemic bupivacaine and 2', 6'-pipecoloxylidide, a key intermediate in the synthesis of bupivacaine, are described. One uses carboxylic acids at high temperature and the other uses water and a cosolvent. The product obtained from the carboxylic acid racemisation is of suitable quality to generate commercial levobupivacaine hydrochloride (Chirocaine) 1 [S], a less cardiotoxic alternative to ...