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

Participants

Reaction Steps

0.295 g of a 50% w/w dispersion of sodium hydride in mineral oil was added to a solution of 1.55 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 21) in 60 ml of dimethylacetamide, whilst ice-cooling and stirring, and the mixture was stirred at the same temperature for 15 minutes. 2.50 g of (S)-1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine were then added to the mixture, whilst ice-cooling, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 6 hours. At the end of this time, 250 ml of ethyl acetate and 150 ml of water were added to the reaction mixture, and the ethyl acetate layer was separated. The aqueous layer was extracted with 50 ml of ethyl acetate once, and the ethyl acetate layer and the extract were combined, washed with a saturated aqueous solution of sodium chloride twice, dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.78 g (yield 96%) of the title compound as a colorless oil.

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