反应详情

561 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 688 mg of 4-hydroxypiperidine hydrochloride in methanol, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, the residue was mixed with tetrahydrofuran, and insoluble materials were filtered off. The filtrate was concentrated by evaporation under reduced pressure, to give a colorless oil, which was dissolved in 20 ml of tetrahydrofuran. 1.02 g of 2-{2-[4-(3,5-dimethoxyphenyl)butyl]phenoxymethyl}oxirane [prepared as described in Example 11(a)] were added to the resulting solution, and the mixture was stirred at 60° C. for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of methylene chloride and methanol as the eluent, to give 1.26 g (yield 95%) of the title compound as a colorless oil.

1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
2. additionthe residue was mixed with tetrahydrofuran, and insoluble materials
3. filtrationwere filtered off
4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
5. customto give a colorless oil, which
6. stirringthe mixture was stirred at 60° C. for 5 hours
7. customAt the end of this time, the solvent was removed by distillation under reduced pressure
8. customthe residue was partitioned between ethyl acetate and water
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. concentrationconcentrated by evaporation under reduced pressure
11. customThe resulting residue was purified by column chromatography through silica gel
12. additionby volume mixture of methylene chloride and methanol as the eluent