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.
Highlights
Histamine is a low-molecular-weight amine derived from the decarboxylation of histidine.It is an important mediator of local immune response as well as many biological processes related to inflammation, gastric acid secretion, and neuromodulation
Only two synthetic methods for the preparation of levocabastine have been reported [16,17]. These processes involve the preparation of key intermediate 6 by chiral resolution, the deprotection of intermediate 5 by electrolysis, and the coupling of piperidine 6 and ketone 7 by reductive amination (Scheme 1)
Considering the previous elegantthe synthesis of levocabastine hydrochloride, we retained hydrochloride, we retained the concept of the previous synthetic strategy, and we focused on the concept of the previous synthetic strategy, and we focused on developing a sustainable synthetic developing a sustainable synthetic procedure for key intermediate and producing the final procedure for key intermediate 5 and producing the final levocabastine with a high optical purity
Summary
Histamine is a low-molecular-weight amine derived from the decarboxylation of histidine. Only two synthetic methods for the preparation of levocabastine have been reported [16,17] These processes involve the preparation of key intermediate 6 by chiral resolution, the deprotection of intermediate 5 by electrolysis, and the coupling of piperidine 6 and ketone 7 by reductive amination (Scheme 1).
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