Multigram-Scale Access to 2-Oxaadamantan-1-amine and 2-Oxaadamantan-1-ol via Optimized Synthesis of Bicyclo[3.3.1]nonane-3,7-dione

Authors

  • Ioann O. Popov Enamine Ltd; Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine https://orcid.org/0009-0007-5366-802X
  • Dmytro M. Volochnyuk Enamine Ltd.; Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; Taras Shevchenko National University of Kyiv; Enamine Scientific Research Institute, Ukraine https://orcid.org/0000-0001-6519-1467

DOI:

https://doi.org/10.24959/ophcj.26.357366

Keywords:

oxaadamantane, bicyclo[3.3.1]nonane-3,7-dione, N,O-acetal, hemiaminal, cage compounds, scale-up synthesis, heteroadamantane, building blocks

Abstract

Practical, tens-of-grams-scale access to 2-oxaadamantan-1-amine and 2-oxaadamantan-1-ol – two overlooked heteroadamantane building blocks of interest for medicinal chemistry – has been achieved through optimization and scale-up of existing literature protocols. The key precursor, bicyclo[3.3.1]nonane-3,7-dione, and both target compounds are obtained in good overall yields using straightforward procedures and standard reagents. Notably, 2-oxaadamantan-1-amine is an exceptionally stable N,O-acetal, in stark contrast to the high hydrolytic lability usually seen in this compound class.

Supporting Agency

  • The work was funded by an internal Enamine grant and the National Research Foundation of Ukraine (grant number 0125U001943, NRFU registration number 2023.03/0250).

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Published

2026-05-01

How to Cite

(1)
Popov, I. O.; Volochnyuk, D. M. Multigram-Scale Access to 2-Oxaadamantan-1-Amine and 2-Oxaadamantan-1-Ol via Optimized Synthesis of Bicyclo[3.3.1]nonane-3,7-Dione. J. Org. Pharm. Chem. 2026, 24, 46-52.

Issue

Vol. 24 No. 1 (2026)

Section

Original Researches

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