Abstract
Reaction of Δ1, 10-hexahydroquinolizine (I) with trichloroacetic acid in benzene afforded 6-chloro-1-azabicyclo [4.4.1] undecan-11-one (II). Acid hydrolysis of II followed by hydrogenation on palladium-charcoal yielded 6-carboxydecahydroazecine (IV), and alkali hydrolysis of II followed by lithium aluminum hydride reduction gave 10-hydroxymethyl-octahydroquinolizine (IX), which was also obtained by lithium aluminum hydride reduction of II. Reaction of II with sodium in liquid ammonia gave both 1-azabicyclo-[4.4.1] undecan-11-ol (XIII) and 6-carbamoyldecahydroazecine (XIV). The action of p-toluenesulfonyl chloride on the latter compound, followed by reduction with lithium aluminum hydride afforded 1-azabicyclo [4.4.1] undecane (XVI).
