Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H₁ Receptor Antagonist.

Abstract

A practical and sustainable method for the synthesis of levocabastine hydrochloride (1), a H₁ receptor antagonist for the treatment of allergic conjunctivitis, that can be applied to the industrial production of the compound has been developed. Substantial improvements over the previously reported procedure are achieved via efficient preparation of an optically active key intermediate (5) without chiral resolution and with a more effective detosylation, which complements the previous procedure. Notably, our process requires no chromatographic purification and provides levocabastine hydrochloride in greater than 99.5% purity in a 14.2% overall yield.

• Authors: Sung Kwon Kang, Dong Hyuk Nam, Jaeseung Ahn, Jaemin Lee, Jaehoon Sim, Jeeyeon Lee, Young-Ger Suh
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 22 Issue 11 (Nov 15 2017) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 29140307 (Publication Type: Journal Article)

Chemical References

• Histamine H1 Antagonists
• Piperidines
• levocabastine

Topics

• Histamine H1 Antagonists (chemical synthesis, chemistry)
• Molecular Structure
• Piperidines (chemical synthesis, chemistry)