Abstract
(−)5′,5′-Dimethylnicotine (I) was synthesized in one step from (—) cotinine; it had approximately 0.03 times the mouse toxicity of nicotine but did not cause the same qualitative toxic signs as nicotine; it stimulated and then depressed autonomic ganglia (anesthetized dog) and directly affected the respiratory center and the cardiovascular system. The total synthesis of 5,5-dimethyl-2-(3-pyridyl)-Δ1-pyrroline (V) and its 1-oxide (VI) was performed. Compound V was hydrogenated to 2,2-dimethyl-5-(3-pyridyl)pyrrolidine (II), and this was converted to its 1-propyl homolog. Compound VI was reduced to 2,2-dimethyl-1-hydroxy-5-(3-pyridyl)pyrrolidine (VIII).
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