Toluene → HCID 19067143, compound

Participants

Reaction Steps

To 10 ml of toluene was dissolved 1.91 g of N-benzyloxycarbonyl-2,6-dimethyl-4-hydroxypiperidine, and to this solution were added 1.70 g of tert-butyl bromoacetate, 0.08 g of tetrabutylammonium sulfate and 1 ml of water, and then aqueous solution of sodium hydroxide in an ice bath. The solution was stirred overnight at room temperature, washed with water and saturated aqueous 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 (100:1 v/v) was obtained 1.11 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-2,6-dimethylpiperidine, which was an oily product (yield: 41%).

Provenance & Evidence