A New Synthesis of rac-Nicotine

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A new synthesis of rac-nicotine was described. For this end the removal of the benzylidene group of 2-substituted 3-benzylidene-1-pyrroline prepared by Sugasawa and Ushioda was first examined. For the best effect, the starting materials ((I) : 2-methyl ; (IXa) : 2-phenyl) were reduced by sodium borohydride and the reduction products were acylated to yield ((IIIa) : 1-acetyl-2-methyl ; (IIIb) : 1-benzoyl-2-methyl ; (XIIa) : 1-benzoyl-2-phenyl). These were cleaved via the corresponding ozonides to yield 3-pyrrolidinones, which were characterized appropriately. This method was successfully extended to 2-(3-pyridyl)-3-benzylidene-1-pyrroline to afford 1-benzoyl-2-(3-pyridyl)-3-pyrrolidinone, whose tosylhydrazone was converted into 1-benzoyl-2-(3-pyridyl)-3-pyrroline according to the method of Bamford and Stevens. The latter was reduced catalytically to rac-nornicotine, from which rac-nicotine was obtained smoothly by Eschweiler-Clark's method.

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