Stereoselective synthesis of (-)-hydroxyclemastine as a versatile intermediate for the H1 receptor antagonist clemastine

Archives of Pharmacal Research

Volumn 30, Issue 12, 2007, Pages 1521-1525

  Jung, Wha Jung ^a   Kim, Hee Doo ^a  

^a Sookmyung Women's University   (South Korea)

Author keywords

Chelation; Clemastine; H1 receptor antagonist; Hydroxyclemastine; Stereoselective

Indexed keywords

EID: 38049178761     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02977320     Document Type: Article

References (11)

1. Ebnother, A. and Weber H. P., Synthesis and absolute configuration of clemastine and its isomers. Helv. Chim. Acta., 59, 2462-2468 (1976).
2. Forrat, V. J., Priesto, O., Ramon, D. J., and Yus, M., trans-1-Sufonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for catalytic enantioselective addition of organozinc reagents to ketones. Chem. Eur. J., 12, 4431-4445 (2006).
3. Goeber, B., Mardini, M. A. A., and Franke, P., Stability and biotransformation of drugs. Part 26. Degradation products of clemastine in solutions. Pharmazie, 43, 539-41 (1988).
4. Jung, J. E., Ho, H., and Kim, H.-D., Bidentate chelation-controlled asymmetric synthesis of α-hydroxy esters based on the glycolate enolate alkylation. Tetrahedron Lett., 41, 1793-1796 (2000).
5. Nelson, W. L., Antihistamines and related antiallergic and antiulcer agents, In Williams, D. A. and Thomas, L. L. (Eds). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins, Philadelphia, pp. 794-818 (2002).
6. Nikiforov, T., Stanchev, S., Milenkov, B., and Dimitrov, V., A route to optically active benzyl ester of (1-methyl-2-pyrrolidinyl) acetic acid, an intermediate in the synthesis of clemastine. Synth. Commun., 20, 1977-1981 (1990).
7. Rhee, H. J., Beom, H. Y., and Kim, H.-D., Stereoselective synthesis of (+)-lauthisan. Tetrahedron Lett., 45, 8019-8022 (2004).
8. Sato, F., Kobayashi, Y., Takahashi, O., Chiba, T., Takeda, Y., and Kusakabe, M., Synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with 2,3-O-isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols. J. Chem. Soc., Chem. Commun., 22, 1636-1638 (1985).
9. Takaoka, M., Optical resolution of clemastine. JP 53012857 (1978).
10. Vanhessche, K. P. M., and Sharpless, K. B., Ligand-dependent reversal of facial selectivity in asymmetric dihydroxylation. J. Org. Chem., 61, 7978-7979 (1996).
11. Vernier, J.-M., El-Abdellaoui, H., Holsenback, H., Cosford, N. D. P., Bleicher, L., barker, G., Bontempi, B., Chavez-Noriega, L., Menzaghi, F., Rao, T. S., Reid, R., Sacaan, A. I., Suto, C., Washburn, M., Lioyd, G. K., and McDonald, I. A., 4-[2-(1-Methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A): A novel cognitive enhancer with selectivity for neuronal nicotinic acetylcholine receptors. J. Med. Chem., 42, 1684-1686 (1999).