A Practical Synthesis of (S)-(-)-Nadifloxacin: Novel Acid-Catalyzed Racemization of Tetrahydroquinaldine Derivative

@inproceedings{Hashimoto1996APS,
  title={A Practical Synthesis of (S)-(-)-Nadifloxacin: Novel Acid-Catalyzed Racemization of Tetrahydroquinaldine Derivative},
  author={Koji Hashimoto and Yoshihiko Okaichi and Daisuke Nomi and Hisashi Miyamoto and Masahiko Bando and Masaru Kido and Tsutomu Fujimura and Takuya Furuta and Jun-ichi Minamikawa},
  year={1996}
}
(S)-(-)-Nadifloxacin [(S)-(-)-9-fluoro-6, 7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H, 5H-benzo[i, j]quinolizine-2-carboxylic acid, (S)-(-)-OPC-7251], an antibacterial agent, was synthesized from (S)-(-)-5, 6-difluoro-2-methyl-1, 2, 3, 4-tetrahydroquinoline (DFTQ), which was prepared by the optical resolution of recemic DFTQ with 2, 3-di-O-benzoxyl-L-tartaric acid. Racemization of the undesired enantiomer [(R)-(+)-DFTQ] was studied in the presence of various acids and the best result… CONTINUE READING

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