Синтез (±)-(1R,6R,7R)-2-азабіцикло[4.2.0]октан-7-олу

• Дата: 2026
• Автори: Nosyk, Danylo A., Lukyanenko, Serhii Yu., Granat, Dmytro S., Yurchenko, Oleksandr O., Grygorenko, Oleksandr O.
• Формат: Стаття
• Мова: Англійська
• Опубліковано: National University of Pharmacy 2026
• Теми: біциклічні сполуки; [2 2] циклоприєднання; лактами; будівельні блоки
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/353627
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

 An approach to the synthesis of (±)-(1R,6R,7R)-2-azabicyclo[4.2.0]octan-7-ol, a promising amino alcohol building block for drug discovery, has been described. The method is based on [2+2] the cycloaddition of tert-butyl vinyl ether and a ketene generated in situ from a glutaric acid derivative, as well as the intramolecular lactam formation as the key steps. Although the [2+2] cycloaddition step and further transformations proceeded without any notable stereoselectivity, the title compound was synthesized in an amount greater than 30 g with a high diastereomeric purity. This was provided by the physical properties of the intermediate (±)-(1R,6R,7R)-7-(tert-butoxy)-2-azabicyclo­[4.2.0]octan-3-one that was easily separated by crystallization.