Dehydropethidine, prepared by the oxidation of pethidine with mercury(II) acetate, has been reduced with lithium aluminium hydride to 2-methyl-5-phenyl-2-aza-7-oxabicyclo[3,2,1]octane (7). The latter reacts with methyl vinyl ketone to give the corresponding 8-(2-acetylethyl)derivative (9), which is in equilibrium with its enamine form (10).
J. W. Lewis and P. A. Mayor, J. Chem. Soc. C, 1970, 1074 DOI: 10.1039/J39700001074
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