Ethyl Acetate → 1-t-Butoxycarbonyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidine

Participants

Reaction Steps

0.965 g of potassium t-butoxide was added to a solution of 1.70 g of 2-[4-(3-methoxyphenyl)butyl]phenol (prepared as described in Preparation 7) in 30 ml of dimethylacetamide, whilst ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. A solution of 3.18 g of 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine in 30 ml of dimethylacetamide was then added dropwise to the solution at the same temperature, and the mixture was stirred at 55° C. for 1.5 hours. At the end of this time, the reaction mixture was cooled, and 200 ml of ethyl acetate and 100 ml of water were added to the mixture, which was then shaken. The ethyl acetate layer was separated, washed twice with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The ethyl acetate layer was then concentrated by distillation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.54 g (yield 95%) of the title compound as a colorless oil.

Provenance & Evidence