1-Bromo-4-phenylmethoxybenzene → (R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester

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(3R)-1-tert-Butoxycarbonyl-3-methylpiperazine (3.0 g, 15.0 mmol), 4-benzyloxybromobenzene (4.73 g, 18.0 mmol), sodium tert-butoxide (2.02 g, 21.0 mmol) and toluene (30 ml) were mixed, and the atmosphere was replaced with nitrogen. tri-tert-Butylphosphine tetrafluoroborate (0.52 g, 1.8 mmol) and palladium acetate (0.34 g, 1.5 mmol) were added thereto and heated at 90 to 100° C. for 4 hours. Water and ethyl acetate were added to the brown reaction mixture, and insoluble matter was removed by filtration. The filtrate was separated into layers. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→50:50) to afford the title compound as a colorless oil (5.29 g, 92%).

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