Abstract
Abstractmagnified imageThe bromination (CuBr2, AcOEt/CHCI3) plus Favorskii rearrangement (EtONa, EtOH) of N‐carbethoxytropinone (4), readily available from tropinone (3), affords mixtures of exo‐ and endo‐isomers of 2,7‐dicarbethoxy‐7‐azabicyclo[2.2.1]heptane (1b) in variable and moderate chemical yield (maximum 37%). The bromination (Br2, HBr/AcOH) reaction of compound 4 gives ethyl trans‐2,4‐dibromo‐3‐oxo‐8‐azabicyclo[3.2.1]octane‐8‐carboxylate (5) in 99% yield, a product that on Favorskii rearrangement (EtONa/EtOH) affords ethyl 2,2‐diethoxy‐3‐oxo‐8‐azabicyclo[3.2.1]octane‐8‐carboxylate in moderate yield (6) (52%).
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