Zhong Bo-hua
2011
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Journal
Chinese Journal of Medicinal Chemistry
Abstract
Levodesmethylphencynonate hydrochloride(1),a novel selective M4 muscarine receptor antagonist,has been chosen as a candidate of anti-Parkinson′s disease drug characterized by its good efficiency,high selectivity and low toxicity.A new synthetic method in the search for more economical and environmental friendly process was developed.The starting compound N,N-diethoxylmethy benzyl amine was prepared by benzyl amine and ethanol,then via Mannich reaction with cyclohexanone,afterwards selective hydrogenation and ester exchange with(R)-methyl-α-phenyl-α-cyclopentyl-α-hydroxy acid ester,hydrogenation,saltization to obtain target compound(1).The overall yield was 8.0%,which increased 10.6% based on common chiral raw material(R)-methyl-α-phenyl-α-cyclopentyl-α-hydroxy acid ester.The chemical structure of levodesmethylphencynonate hydrochloride was characterized by MS,1H-NMR and element analysis.Compared with the original synthetic process,the new route is facile and suitable for industrialized production with lower cost,lower pollution and higher yield.