反应详情

温度

80 °C

1.18 g (4.29 mmol) of diphenylphosphoryl azide and 434 mg (4.29 mmol) of triethylamine were added to 30 mL of a tert-butanol suspension comprising 1.0 g (3.9 mmol) of 4-(adamantan-1-yl)benzoic acid at 0° C. The mixture was stirred at 80° C. for 4.5 hours, and 40 mL of THF was added. The mixture was stirred for an additional 2 hours. Thereafter, the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, and the resultant was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline in this order. The resultant was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 679 mg of tert-butyl [4-(adamantan-1-yl)phenyl]carbamate (yield: 53%).

1. stirringThe mixture was stirred for an additional 2 hours
2. distillationThereafter, the solvent was distilled off under reduced pressure
3. additionEthyl acetate was added to the residue
4. washthe resultant was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline in this order
5. dry with materialThe resultant was dried over anhydrous sodium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe obtained crude product
8. customwas separated
9. custompurified by silica gel column chromatography