3-(1-Methylpyrrolidin-2-yl)pyridine → (R)-Nicotine

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Several resolving agents, solvents and their combinations were studied to resolve the synthetically obtained racemic nicotine. When the naturally available d-tartaric acid was used as the resolving agent, only the unnatural (R)-nicotine was obtained with low chiral purity (62%). When l-tartaric acid was used (S)-nicotine was obtained. Although its chiral purity was high (98.3%), the yield was very low (29%). When di-p-toluoyl-d-tartaric acid was used, (S)-nicotine was obtained in 60% yield with 88% chiral purity. When di-p-toluoyl-l-tartaric acid was used, (R)-nicotine was obtained in 15% yield with 94.7% chiral purity. In all the above cases, either the yield or the chiral purity was not satisfactory. We also studied dibenzoyl-d-tartaric acid as a resolving agent in different solvents (Table.1).

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