反应详情

To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzaldehyde (500 mg) in methylene chloride (10 ml) was added 70% 3-chloroperbenzoic acid (712 mg) with ice-cooling, and the mixture was stirred at room temperature for 4.5 hours. After completion of the reaction, aqueous sodium hydrogencarbonate solution and aqueous sodium thiosulfate solution were added, and the mixture was extracted with methylene chloride and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was dissolved in methanol (3.4 ml) and thereto was added 1N aqueous sodium hydroxide solution (1.7 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10% aqueous citric acid solution was added, and the mixture was extracted with chloroform and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained solid was washed with diethyl ether and dried under reduced pressure to give the title compound (350 mg).

1. temperaturecooling
2. additionwere added
3. extractionthe mixture was extracted with methylene chloride
4. washwashed successively with water and saturated brine
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. customthe solvent was evaporated
7. dissolutionThe obtained residue was dissolved in methanol (3.4 ml)
8. additionwas added 1N aqueous sodium hydroxide solution (1.7 ml)
9. stirringthe mixture was stirred at room temperature for 1 hour
10. customAfter completion of the reaction, 10% aqueous citric acid solution
11. additionwas added
12. extractionthe mixture was extracted with chloroform
13. washwashed successively with water and saturated brine
14. dry with materialThe organic layer was dried over anhydrous sodium sulfate
15. customthe solvent was evaporated
16. washThe obtained solid was washed with diethyl ether
17. customdried under reduced pressure