Water → HCID 19067200, compound

Participants

Reaction Steps

2.53 g of N-benzyloxycarbonyl-4-hydroxy-3-methyl-piperidine was dissolved in 20 ml of toluene, and to this solution was added 2.96 g of tert-butyl bromoacetate, 0.1 g of tetrabutylammonium sulfate and 1 ml of water. Aqueous solution (10.1 g) of sodium hydroxide was added dropwise to this solution in an ice bath, and the solution was stirred overnight at room temperature. The resulting solution was washed with water and saturated solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:3 v/v) was obtained 1.59 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-3-methylpiperidine, which was an oily product (yield: 44%).

Provenance & Evidence