2-Tert-butyl 5-methyl pyridine-2,5-dicarboxylate → Piperidine-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester

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Reaction Steps

Pyridine-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester (5.8 g, 24.45 mmol) was dissolved in glacial acetic acid (30 mL) and hydrogenated at 50-60 psi for 3 days with 10% palladium on carbon catalyst (0.6 g). The reaction mixture was filtered through a pad of Celite which was then washed with methanol. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in water (100 mL) and solid sodium carbonate (15 g) was added to bring the pH to 8. The solution was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (5.2 g, 87%).

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