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Chemical Journal of Chinese Universities 1988, Vol. 9 Issue (7) :743-745    DOI:
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Synthesis of S- and R-Timolol Maleate
Zhou Zhishan, Zhu Juliang
Department of Medicinal Chemistry, School of Pharmacy, Shanghai Medical University, Shanghai

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Abstract The S- and R-timblol were prepared by optical resolution of racemic timolol. Thus, the treatment of glycerol with HCl afforded 3-chloro-l,2-propanediol(1). 1 undergoes condensation with tertiary butylamine to give dl-3-t-butylamino-1, 2-propanediol(2) in 70.9% yield. The treatment of 2 with benzaldehyde afforded the oxazolidine derivative(3) in 79% yield. Racemic timolol(4) could be obtained in 53% yield from 3 by treatment with 3-chloro-4-morpholino-1,2,5-thiadiazole and t-BuOKin t-BuOHand hydrolization. 4 is resolved with d-tartaric acid to give S-timolol-d-tartaric acid . salt and R-timolol-d-tartaric acid salt. Then the treatment of these salts with NaOHand maleic acid afforded S-timolol and R-timolol maleate, respectively.
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KeywordsTimolol   R-Timolol   β-adrenoceptor blocker   Optical resolution     
Received 1987-01-13; published 1988-07-24
Cite this article:   
Zhou Zhishan, Zhu Juliang.Synthesis of S- and R-Timolol Maleate[J]  Chemical Journal of Chinese Universities, 1988,V9(7): 743-745
http://www.cjcu.jlu.edu.cn//EN/     or     http://www.cjcu.jlu.edu.cn//EN/Y1988/V9/I7/743
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