反应详情

温度

100 °C

8-(4-Octylphenyl)-7-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (0.5 g, 1.452 mmol) and sodium hydroxide (10.89 ml, 21.77 mmol) were combined in water (8.54 ml) and equipped with a reflux condensor. The mixture was heated at about 100° C. for about 72 h. The reaction was cooled and acidified with concentrated HCl until pH=4-5. The product was collected by vacuum filtration and dried under vacuum. The residue was purified by flash column chromatography (1″×6″ of silica) eluting with 1:1 EtOAc/(6:3:1 CHCl3/MeOH/NH4OH). The product fractions were combined. The solvents were removed under reduced pressure and the residue triturated with ether. The resulting solid was collected by vacuum filtration and washed with ether to provide 3-amino-5-(4-octylphenyl)tetrahydrofuran-3-carboxylic acid (0.280 g, 0.877 mmol, 60.4% yield) as a white solid:

1. customequipped with a reflux condensor
2. temperatureThe reaction was cooled
3. filtrationThe product was collected by vacuum filtration
4. customdried under vacuum
5. customThe residue was purified by flash column chromatography (1″×6″ of silica)
6. washeluting with 1:1 EtOAc/(6:3:1 CHCl3/MeOH/NH4OH)
7. customThe solvents were removed under reduced pressure
8. customthe residue triturated with ether
9. filtrationThe resulting solid was collected by vacuum filtration
10. washwashed with ether