(R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydro-2H-pyran-4-yloxy)pyridine → (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine di-p-toluoyl-D-tartrate

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To a stirred solution of (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine (4.0 g, 15 mmol) in ethanol (12.5 mL) solution, heated to 60° C., was added solid di-p-toluoyl-D-tartaric acid (5.3 g, 14 mmol). The solution was held at 60° C. for 2-3 min to ensure complete dissolution of the solids, then the heat source was removed and the solution was cooled to 25-30° C. over 60 min. The resulting suspension was held at 25-30° C. for 30 min, and then filtered to collect the solids. The solids were washed with ethanol (2×20 mL), air dried for 30 min, then dried in a vacuum oven under reduced pressure at 50° C., until a constant weight was established, to give (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine di-p-toluoyl-D-tartrate as an off-white solid (6.7 g, 72%). NNNMR analysis indicated a 1:1 salt stoichiometry. 1H-NMR (DMSO-d6, 400 MHz) δ 8.18 (s, 1 H), 8.15 (s, 1 H), 7.86 (d, 4 H), 7.47 (s, 1 H), 7.32 (d, 4 H), 6.43 (d, 1 H), 6.36 (m, 1 H), 5.67 (s, 2 H), 4.69 (m, 1 H), 3.85 (m, 2 H), 3.49 (m, 2 H), 3.25 (m, 2 H), 3.10 (m, 1 H), 2.88 (m, 2 H), 2.39 (s, 6 H), 1.98 (m, 3 H), 1.60 (m, 3 H).

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