Multigram Synthesis of 2-Azabicyclo[2.1.1]hexane-1-Carboxylates (2,4-Methanoprolines) – Promising Bicyclic Proline Analogs
An optimized approach towards 4-substituted 2,4-methanoproline derivatives is reported. Careful selection of the starting materials and optimized isolation procedure provided easy access to a key bicyclic building block in a preparative yield of 32% over five laboratory steps of up to 0.7 kg. Further modifications allowed us to obtain a number of useful derivatives, including those containing NH2, COOH, CH2NH2, and CH2F fragments with orthogonally protected functionalities.
Authors
- Oleksandr S. Liashuk (ORCID: https://orcid.org/0000-0002-2677-435X)
- Oleksandr O. Grygorenko (ORCID: https://orcid.org/0000-0002-6036-5859)
- Anton V. Chernykh (ORCID: https://orcid.org/0000-0002-2292-4138)
- Dmitriy M. Volochnyuk (ORCID: https://orcid.org/0000-0001-6519-1467)
- Anastasiia M. Hurieva
Institutions
- National Academy of Sciences of Ukraine (UA)
- Taras Shevchenko National University of Kyiv (UA)
- Institute of Organic Chemistry (UA)
- Enamine (Ukraine) (UA)
Publication Details
- Journal
- Journal of organic and pharmaceutical chemistry
- Published
- 2024-12-23
- DOI
- https://doi.org/10.24959/ophcj.24.314843
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.23
Funders
- National Academy of Sciences of Ukraine
- Ministry of Education and Science of Ukraine
- Enamine
- Taras Shevchenko National University of Kyiv