Treatment of the 2-azabicyclo[2.2.2]oct-5-ene imino Diels–Alder adduct (2) with N-bromosuccinimide in aqueous dimethoxyethane gives the rearranged bromohydrin (4a), whose structure is confirmed by X-ray crystallographic analysis, and which serves as a precursor to the 6-azabicyclo[3.2.1]octane-4-one (7).
A. B. Holmes, P. R. Raithby, J. Thompson, A. J. G. Baxter and J. Dixon, J. Chem. Soc., Chem. Commun., 1983, 1490 DOI: 10.1039/C39830001490
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