Generation of 1-Azabicyclo[3.2.1]Octane and 5-Azatricyclo[3.2.1.02,7]Octane Systems by Carbenium Ion Rearrangements during Production of the Antihistamine Drug Quifenadine
Tetrahedron Letters
2020
Mikus Puriņš,
Viktors Kumpiņš,
M. Skomorokhov,
Anatolijs Mišņovs,
Māris Turks
Dehydration of ethyl 3-hydroxyquinuclidine-3-carboxylate is one of the key steps during production of the antihistamine drug Quifenadine (Phencarol). The side products of this process were isolated and their structures proved using NMR spectroscopy. Carbenium ion rearrangements of quinuclidine-3-carboxylate gave rise to 1-azabicyclo[3.2.1]octane and 5-azatricyclo[3.2.1.02,7]octane systems, which serve as impurity standards for the manufacturing process of Quifenadine and are also interesting building blocks for medicinal chemistry.
Keywords
Cationic rearrangement, Protonated cyclopropane, Quifenadine, Quinuclidine
DOI
10.1016/j.tetlet.2019.151405
Hyperlink
https://www.sciencedirect.com/science/article/pii/S0040403919311967?via%3Dihub
Puriņš, M., Kumpiņš, V., Skomorokhov, M., Mišņovs, A., Turks, M. Generation of 1-Azabicyclo[3.2.1]Octane and 5-Azatricyclo[3.2.1.02,7]Octane Systems by Carbenium Ion Rearrangements during Production of the Antihistamine Drug Quifenadine. Tetrahedron Letters, 2019, Vol. 61, No. 3, Article number 151405. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2019.151405
Publication language
English (en)