An efficient procedure for the resolution of α-cyano-α-fluoro- p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2- indanol esters

Tomoya Fujiwara, Masaki Sasaki, Kenji Omata, Chizuko Kabuto, Kuninobu Kabuto, Yoshio Takeuchi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Development of a new, efficient resolution method of α-cyano-α- fluoro-p-tolylacetic acid (CFTA) 2a has been successfully achieved, which has been troublesome to obtain by conventional methods, in spite of its outstanding ability as an NMR chiral derivatizing agent. Fractional recrystallization of a mixture of the diastereomeric CFTA esters prepared from racemic CFTA chloride and (1R,2S)-N-carbobenzyloxy-cis-1-amino-2-indanol (-)-B afforded the less-soluble diastereomer, which was hydrolyzed to give (S)-2a. It has also been demonstrated that optically active N-acetyl-cis-1-amino-2-indanol is effective for the chromatographic resolution of α-arylacetic acids including ibuprofen and naproxen.

Original languageEnglish
Pages (from-to)555-563
Number of pages9
JournalTetrahedron Asymmetry
Volume15
Issue number3
DOIs
Publication statusPublished - 2004 Feb 9

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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