Синтез (±)-(1R,6R,7R)-2-азабіцикло[4.2.0]октан-7-олу
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...
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| Datum: | 2026 |
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| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | Englisch |
| Veröffentlicht: |
National University of Pharmacy
2026
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| Schlagworte: | |
| Online Zugang: | https://ophcj.nuph.edu.ua/article/view/353627 |
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| Назва журналу: | Journal of Organic and Pharmaceutical Chemistry |
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Journal of Organic and Pharmaceutical Chemistry| Zusammenfassung: | 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. |
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| DOI: | 10.24959/ophcj.26.353627 |