1 / 1

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. Reaction 1 Synthesis of gem -dimethyl ester 9 via successive bis -alkylation of 8 Reaction 2

jeneva
Télécharger la présentation

The Multistep Synthesis of Fexofenadine

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Chem 213H: Organic Chemistry Lab • Department of Chemistry, Pennsylvania State University Dr. Masters & AnthonyNocket Christopher Mallis, Leon Lin, Kayla Shellhammer Reaction 1 Synthesis of gem-dimethyl ester 9 viasuccessive bis-alkylation of 8 Reaction 2 Synthesis of benzylic bromide 10 viaWohl-Ziegler Brominationof 9 Reaction 3 Synthesis of ester aldehyde 7 viaSommelet Oxidation of 10 Reaction 4 Synthesis of alcohol 5 viaGrignard addition of 6 to 7 Reaction 5 Synthesis of lactol3a viaacid-catalyzed transacetalization of 5 Conclusion 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. Acknowledgements 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. References 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. Chem213H Lab Guide, Spring 2013 Edition. Background Fexofenadine is an anti-histamine drug used to treat allergy symptoms. It works by blocking the H1histamine receptor. Fexofenadine is the active ingredient in Allegra. The objective for this project was to perform a multistep synthesis of fexofenadine. The Multistep Synthesis of Fexofenadine Fexofenadine www.sigmaaldrich.com Retrosynthetic Scheme for Fexofenadine Synthesis Scheme 1 Scheme 2 Scheme 3 bis -alkylation Wohl-Zeigler Bromination Sommelet Oxidation Synthetic Route Scheme 4 Scheme 5 Scheme 6 Scheme 7

More Related