Construction of Diarylmethane Compounds. Synthesis of tolpropamine via Heck-Matsuda Reaction

Construction of Diarylmethane Compounds. Synthesis of tolpropamine via Heck-Matsuda Reaction

Silva, Allan Ribeiro da; Prediger, Patrícia; Correia, Carlos Roque Duarte

Abstract:

Tolpopramine is a antihistamine and antipruritic drug used for skin diseases treatment such as allergy and itch. Previous syntheses relied on the Witting reaction to obtain 1-phenyl-1-(p-tolyl)ethane followed by hydroaminomethylation reaction using rhodium catalysis. This methodology does not provide conditions for an enantiosselective reaction. The compound 1 could be easily obtained from two Heck-Matsuda reactions from the N-protected allylamine 3.

Tolpopramine is a antihistamine and antipruritic drug used for skin diseases treatment such as allergy and itch. Previous syntheses relied on the Witting reaction to obtain 1-phenyl-1-(p-tolyl)ethane followed by hydroaminomethylation reaction using rhodium catalysis. This methodology does not provide conditions for an enantiosselective reaction. The compound 1 could be easily obtained from two Heck-Matsuda reactions from the N-protected allylamine 3.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013818131420

Referências bibliográficas

• [1] 1 Li, S., Huang, K., Zhang, J., Wu, W., Zhang, X. Org. Lett. 2013, 15, 1036
• [2] 2 Prediger, P., Barbosa, L. S. F.; G Correia, C. R. D. J. Org.
• [3] Chem. 2011, 76, 7737.
• [4] 3 Taylor, J. G.; Correia, C. R. D. J. Org. Chem 2011, 76, 857.

Como citar:

Silva, Allan Ribeiro da; Prediger, Patrícia; Correia, Carlos Roque Duarte; "Construction of Diarylmethane Compounds. Synthesis of tolpropamine via Heck-Matsuda Reaction", p-162-162. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013818131420