Abstract
The mercuric acetate-(ethylenedinitrilo) tetraacetic acid oxidation of aminoalcohol III furnished lactamalcohol V in 73% yield and its O-acetyl derivative (VI) as a minor product. Treatment of V with phosphoryl chloride gave tetrahydrobenzo [α] quinolizinium salt X in 87% yield, whereas hydrogenolysis of V in the presence of perchloric acid and ring-closure of the resulting lactam VIII afforded hexahydrobenzo [α] quinolizinium salt IX, which produced benzo [α] quinolizidine Ia on hydrogenation. When treated with perchlo-ric acid, lactamalcohol V yielded oxazolinium salt VIIa in a good yield. The facile hydrogenolysis of VIIa to VIII has suggested the possibility that the perchloric acid-accelerated, direct hydrogenolysis of V may proceed through VIIa. The starting aminoalcohol III was synthesized either by the sodium borohydride reduction of aminoketone II obtained from piperidine and 3, 4-dimethoxyphenacyl bromide or by reduction of quaternary salt IV from pyridine and 3, 4-dimethoxyphenacyl bromide.
