Optimization of the Synthesis of 2-Adamantanecarboxylic Acid
Научная публикация
| Общая информация |
Язык:
Английский,
Жанр:
Статья (Full article),
Статус опубликования:
Опубликована,
Оригинальность:
Переводная
|
| Журнал |
Chemistry for Sustainable Development
ISSN: 1817-1818
|
| Вых. Данные |
Год: 2022,
Том: 30,
Номер: 6,
Страницы: 612-616
Страниц
: 5
DOI:
10.15372/csd2022424
|
| Ключевые слова |
words: adamantane, biological activity, Corey–Chaykovsky reaction |
| Авторы |
Munkuev A.A.
1
,
Sheshkovas A.Zh.
2
,
Suslov E.V.
1
,
Volcho K.P.
1
,
Salakhutdinov N.F.
1
|
| Организации |
| 1 |
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Novosibirsk, Russia
|
| 2 |
Novosibirsk State University, Novosibirsk, Russia
|
|
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 %.