Cl[C:2]1[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCOCC1.C(Cl)Cl>[C:28]1([NH:27][C:2]2[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1A solution of 1-(2-chloro-pyridin-3-yl)-propan-1-one (6.0 g, 35.4 mmol) in 1,4-dioxane (59.0 mL) in a high pressure reaction tube was treated with (1S)-(+)-10-camphorsulfonic acid (20.5 g, 88.4 mmol). The resulting mixture was heated to 70° C. until all of the solids went into solution. The reaction was raised out of the heating bath, opened and treated with aniline (4.94 g, 4.84 mL, 53.1 mmol). The vessel was then re-sealed and heated at 95° C. overnight. After cooling to room temperature, the reaction was diluted with methylene chloride (75 mL) and was washed with a saturated aqueous sodium bicarbonate solution (2×100 mL). The organics were then dried over sodium sulfate, filtered, concentrated in vacuo and dried under high vacuum. The residue was then recrystallized from methanol. Collection by filtration (washing with 10 mL of methanol and 30 mL of hexanes) afforded 1-(2-phenylamino-pyridin-3-yl)-propan-1-one (5.64 g) of the desired product as a yellow, crystalline solid. The mother liquor was dry loaded onto silica gel. Flash chromatography (40 g, 10-25% ethyl acetate-hexanes) afforded an additional amount (1.28 g, 86% total yield) of the desired product as a yellow solid.
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