Sodium Bicarbonate → 5-[1-(2-Fluoro-2-methyl-propyl)-piperidin-4-ylmethoxy]-1'-methanesulfonyl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl

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To a solution of 2-methyl-1-[4-[[6-(1-methylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-pyridyl]oxymethyl]-1-piperidyl]propan-2-ol (33 g; 77.91 mmoles) in dichloromethane (155 mL) is added bis(2-methoxyethyl)aminosulfur trifluoride (16.63 mL; 85.70 mmoles) at an internal temperature of 22-23° C. The reaction is stirred at 25° C. for 2 h. Aqueous saturated solution of sodium bicarbonate is added to pH 7. Layers are separated, the aqueous layer is extracted with dichloromethane (2×500 mL), the combined organic layers are dried over magnesium sulphate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with 98:2 dichloromethane:methanol. The solid is triturated with 500 mL of methyl t-butyl ether and filtered. The solid is dried in an oven at 40° C. for 3 days to obtain 24 g of the title compound as a white solid. MS (m/z) 426 (M+1).

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