Water → Benzyl (2s)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a solution (15 mL) of benzyl((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-1-methylpentyl)carbamate (430 mg) in tetrahydrofuran were added triethylamine (0.235 mL) and methanesulfonyl chloride (0.105 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (20 mL). Potassium tert-butoxide (152 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 0.1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→2:1) to give the title compound (yield: 260 mg) as a colorless oil.

Provenance & Evidence