To a mixed solution of 5-methyl-6-[4-(morpholin-4-yl]cyclohex-1-en-1-yl)pyridin-3-amine (9.5 g) described in Reference Example 108, potassium fluoride (8.07 g), palladium(II) acetate (1.56 g), water (35 ml) and tetrahydrofuran (81 ml) was added poly(methylhydrosiloxane) (6.4 ml) at water temperature, and then stirred at room temperature for 2 hours. The solvent of the reaction solution was evaporated in vacuo, and the residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give the titled compounds cis-5-methyl-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (3.4 g, MS (ESI) m/z: 276 (M+H)+) and trans-5-methyl-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (2.4 g, MS (ESI) m/z: 276 (M+H)+) as white solids respectively.
