Abstract: To date, compounds having an adamantane moiety have found wide application in the pharmaceutical industry. Despite the fact that most biologically active adamantyl-bearing derivatives contain substituents in the first position of the adamantane molecule, some derivatives with substituents in the second position have also shown valuable pharmacological properties. While 1-adamantanecarboxylic acid is an inexpensive and commercially available reagent, its 2-substituted analogue is substantially less available, and therefore, the development and optimization of approaches to the synthesis of 2-adamantanecarboxylic acid are of great importance. In this work, a three-stage method for the synthesis of 2-adamantanecarboxylic acid has been optimized, based on the Corey-Chaykovsky reaction of 2-adamantanone with trimethylsulphoxonium iodide in the presence of potassium hydroxide, followed by acid-catalyzed opening of the oxirane ring and oxidation of aldehyde 9 to the target carboxylic acid. The total yield of the target product is 70 %.

Cite: Munkuev A.A. , Sheshkovas A.Z. , Suslov E.V. , Volcho K.P. , Salakhutdinov N.F.
Optimization of the Synthesis of 2-Adamantanecarboxylic Acid
Chemistry for Sustainable Development. 2022. V.30. N6. P.612-616. DOI: 10.15372/csd2022424 WOS OpenAlex

Original: Мункуев А.А. , Шешковас А.Ж. , Суслов Е.В. , Волчо К.П. , Салахутдинов Н.Ф.
Оптимизация метода синтеза 2-адамантанкарбоновой кислоты
Химия в интересах устойчивого развития. 2022. Т.30. №6. С.632-636. DOI: 10.15372/KhUR2022424AN OpenAlex

Identifiers:

Web of science:	WOS:000898671800001
OpenAlex:	W4312555028

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