Imidazole → 1-Benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)piperidin-4-one

Participants

Reaction Steps

0.82 g of imidazole and 0.72 g of tert-butyldimethylchlorosilane were added to N,N-dimethylformamide (10 mL) solution of 1.0 g of methyl 1-benzyl-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate, and stirred at room temperature for 0.5 hours, and then methanol was added thereto. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline water in that order, dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was dissolved in 30 mL of diethyl ether, and with cooling with ice, 0.30 g of lithiumaluminium hydride was added thereto, and stirred at that temperature for 1.5 hours, and then methanol was added thereto. The reaction solution was diluted with ethyl acetate, then washed with water and saturated saline water in that order, dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. High-polarity side products were removed from the resulting residue through silica gel column chromatography (chloroform/methanol=10/1), and the residue was dissolved in 10 mL of N,N-dimethylformamide, and 0.41 g of imidazole and 0.72 g of tert-butyldimethylchlorosilane were added thereto, and stirred at room temperature for 10 minutes. Water was added to the reaction solution, and diluted with ethyl acetate. Then, this was washed with water and saturated saline water in that order, dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=10/1 to 4/1) to obtain 566 mg of the entitled compound as a pale yellow oily substance.

Provenance & Evidence