A large-scale synthesis of enantiomerically pure cetirizine dihydrochloride using preparative chiral HPLC

Organic Process Research and Development

Volumn 5, Issue 2, 2001, Pages 110-115

  Pflum, Derek A ^a   Wilkinson, H Scott ^a   Tanoury, Gerald J ^a   Kessler, Donald W ^a,b   Kraus, Hali B ^a,b   Senanayake, Chris H ^a   Wald, Stephen A ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

^b Department of Analytical Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035532805     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0002951     Document Type: Article

References (6)

1. Opalka, C. J.; D'Ambra, T. E.; Faccone, J. J.; Bodson, G.; Cossement, E. Synthesis 1995, 766.
2. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837.
3. Pflum, D. A.; Wald, S. A.; Senanayake, C. H. Synthesis of Enantiomerically Enriched Cetirizine. Presented at the 219th National Meeting of the American Chemical Society, San Francisco, CA, April, 2000; Paper ORGN 62. Manuscript in preparation.
4. Cetirizine dihydrochloride is inexpensive ($100/kg) and widely available. The material used in this study was purchased from Bombay Drugs & Pharmas, Ltd.
5. The large-scale synthesis of racemic 5 and chiral HPLC separation were performed by Regis Technologies, 8210 Austin Ave, Morton Grove, IL 60053. The large-scale chiral HPLC was performed using an automated, computer-controlled isocratic/gradient preparative HPLC system and a Prochem LC150 column (40 × 15 cm) packed with Chiralpak AD packing material (2 kg).
6. The absolute stereochemistry has been assigned by single-crystal X-ray analysis. See ref 2 and Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153.