Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4837-4840

  Corey, E J ^a   Helal, Christopher J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIHISTAMINIC AGENT; BENZHYDRYL DERIVATIVE; CETIRIZINE; CHLOROBENZENE; CHROMIUM DERIVATIVE; HISTAMINE H1 RECEPTOR ANTAGONIST;

ARTICLE; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0030575358     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00964-1     Document Type: Article

References (17)

1. 1. The Merck Index, 11th ed.; Budavari, S.; Merck & Co.: Rahway, N. J. 1989, p. 310.
2. 2. Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993, 46, 1055.
3. 3. Opalka, C. J.; D'Ambra, T. E.; Faccone, J. J.; Bodson, G.; Cossement, E. Synthesis 1995, 766.
4. 4. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153.
5. 3: Jaouen, G. In Transition Metal Organometallics in Organic Synthesis Vol II., Alper, H., Ed.; Academic Press, New York, 1978, Chapter 2.
6. 6. (a) Semmelhack, M. F.; Bisaha, J.; Czarny, M. J. Am. Chem. Soc. 1979, 107, 768.
7. (b) Beswick, P. J.; Leach, S. J.; Masters, N. F.; Widdowson, D. A. J. Chem. Soc., Chem. Commun. 1984, 46.
8. 3).
9. 4]: 353.9751; found: 353.9763.
10. 2, EtOAc, 98%).
11. t: 30.35 min, major; 44.17 min, minor).
12. 11. (a) Uemura, M.; Minami, T.; Isobe, K.; Kobayashi, T.; Hayashi, Y. Tetrahedron Lett. 1986, 27, 967.
13. (b) Top, S.; Jaouen, G. J. Org. Chem. 1981, 46, 78.
14. 12. Carganico, G.; Del Buttero, P.; Maiorana, S.; Riccardi, G. J. Chem. Soc., Chem. Comm. 1978, 989.
15. 2O) δ 7.46 (m, 4H), 7.33 (m, 5H), 5.10 (s, 1H), 4.06 (s, 2H), 3.77 (t, J=4.4 Hz, 2H), 3.51 (br s, 4H), 3.37 (t, J=4.5 Hz, 2H), 3.23 (br s, 4H) ppm.
16. 14. We are indebted to Dr. C. J. Opalka at Albany Molecular Research, Inc., for an authentic sample of (-)-cetirizine hydrochloride.
17. 15. This research was assisted financially by a grant from the National Science Foundation and a fellowship to C.J.H.(NSF).