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The Multistep Synthesis of Fexofenadine
Chem 213H: Organic Chemistry Lab
Department of Chemistry, Pennsylvania State University
Dr. Masters & Anthony Nocket
Christopher Mallis, Leon Lin, Kayla Shellhammer
Fexofenadine is an anti-histamine drug used to treat allergy symptoms. It
works by blocking the H1 histamine receptor. Fexofenadine is the active
ingredient in Allegra. The objective for this project was to perform a
multistep synthesis of fexofenadine.
Reaction 1
Synthesis of gem-dimethyl ester 9 via successive bis-alkylation of 8
Reaction 4
Synthesis of alcohol 5 via Grignard addition of 6 to 7
Retrosynthetic Scheme for Fexofenadine Synthesis
Scheme 1
Reaction 2
Synthesis of benzylic bromide 10 via Wohl-Ziegler Bromination of 9
Reaction 5
Synthesis of lactol 3a via acid-catalyzed transacetalization of 5
Scheme 2
Scheme 3
Synthetic Route
Scheme 4
Scheme 5
Scheme 6
Scheme 7
bis -alkylation
Reaction 3
Synthesis of ester aldehyde 7 via Sommelet Oxidation of 10
This synthetic pathway was successful until the Grignard addition. Starting
from 8, 9 was synthesized with a 52% yield. Using 9, 10 was synthesized with a
78% yield. Ester aldehyde 7 was synthesized with a 10% yield. A Grignard
addition was then performed on 7, but it did not yield a pure product. Overall, the
synthesis was fairly successful, and with more time Fexofenadine probably could
have been successfully synthesized.
The authors would like to acknowledge Penn State University for the use of
their lab and materials. The authors would also like to acknowledge Katherine
Masters and Anthony Nocket for their assistance in the lab.
inter alia: (a) Kawai, S. H.; Hambalek, R. J.; Just, G. J. Org. Chem. 1994, 59, 2620-2622. (b) Ronggeng, W.;
Yougui, Z.; Guancho, Z. Res. Chem. Intermed. 2012. (c) Raghavendra, G. M.; Harsha, K. B.; Vinaya, K.;
Mantelingu, K.; Rangappa, K. S. Synth. Commun. 2011, 41, 2296-2303. Huang, J.; Wang, W.; Wang, L.-X. Org.
Proc. Res. Dev. 2010, 14, 1464-1468.
(a) Fang, Q. K.; Senanayake, C. H.; Wilkinson, H. C.; Wald, S. A.; Li, H. Tetrahedron Lett. 1998, 39, 2701-2704.
(b) Yu, S.; Tang, L-H; Tao, L.; Qin, X-F. Chin. J. Pharm. 2006, 37, 439-440.
Masters, K.M. Chem 213H Lab Guide, Spring 2013 Edition.
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