Myosmine → 3-(Pyrrolidin-2-yl)pyridine

Participants

Reaction Steps

(J. Org. Chem., 1982, 47, 4165-4167). Hatton et al. used palladium on activated carbon in methanol to reduce myosmine labeled with stable isotope, [6−2H]-myosmine to [6−2H]-nornicotine (J. Label Compd. Radiopharm. 2009, 52, 117-122). After screening a number of catalysts, we selected palladium on carbon with methanol as medium. After general workup, the pure (R,S)-nornicotine was isolated by high vacuum distillation in high yields and high purity. Conversion of (R,S)-nornicotine to (R,S)-nicotine was carried out by N-methylation using formaldehyde and formic acid as reported in the literature (J. Amer. Chem. Soc., 1993, 115, 381-387).

Provenance & Evidence