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

Participants

Reaction Steps

A mixture of dibenzoyl-l-tartaric acid (58 g, 0.154 mol), 100 ml isopropanol and (R,S)-nicotine (25 g, 0.154 mol) was stirred for 1 hr and heated to reflux. While refluxing, 50 ml methanol was added and continued as in Example 1 to get (R)-nicotine (7.2 g, 57.6% yield) 99.85% GC, optical rotation: +141°, 99.9% chiral purity by HPLC.

Provenance & Evidence