Hexane → t-Butyl 4-[4-(4-amino-2-fluorophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate

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To a solution of a crude product of t-butyl 4-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate (548 mg) in methanol (50 ml) was added 10% palladium carbon (100 mg), followed by stirring under a hydrogen atmosphere at room temperature for 2 hrs. The catalyst was filtered. The filtrate was concentrated under a reduced pressure to give a residue, which was then subjected to silica gel column chromatography (Fuji Silysia BW-300, eluent; hexane:ethyl acetate=1:1 to 1:2, then ethyl acetate) to provide a mixture of the starting material and the target compound. The mixture was dissolved in methanol (50 ml) again, and then 10% palladium carbon (100 mg) was added thereto, followed by stirring under a hydrogen atmosphere at room temperature for 2 hrs. The catalyst was filtered. The filtrate was concentrated under a reduced pressure to give a residue, which was then filtered by silica gel. The filtrate was concentrate under a reduced pressure to provide the titled compound (185 mg) as a yellow oil.

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