反应详情

N-Boc-4-piperidinol (10 g, 50 mmol), 4-nitrophenol (7.0 g, 50 mmol) and triphenylphosphine (15.7 g, 60 mmol) were dissolved in dry tetrahydrofuran (150 mL), and cooled on the ice bath. Diisopropyl azodicarboxylate (11.8 mL, 60 mmol) was added slowly, and stirred for 2 days at room temperature. The solvent was distilled off under reduced pressure, diethyl ether was added, and the solid precipitate was filtered off. The filtrate was concentrated and the product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1). Trifluoroacetic acid was added to the obtained residue and stirred at room temperature for 1 hour. After distillation under reduced pressure, 1N sodium hydroxide aqueous solution was added, and the mixture extracted with ethyl acetate. After drying with anhydrous sodium sulfate, the product was concentrated and dried to obtain the target substance (6.75 g, 61%).

1. distillationThe solvent was distilled off under reduced pressure, diethyl ether
2. additionwas added
3. filtrationthe solid precipitate was filtered off
4. concentrationThe filtrate was concentrated
5. customthe product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)
6. additionTrifluoroacetic acid was added to the obtained residue
7. stirringstirred at room temperature for 1 hour
8. distillationAfter distillation under reduced pressure, 1N sodium hydroxide aqueous solution
9. additionwas added
10. extractionthe mixture extracted with ethyl acetate
11. dry with materialAfter drying with anhydrous sodium sulfate
12. concentrationthe product was concentrated
13. customdried
14. customto obtain the target substance (6.75 g, 61%)