tert-Butanol → Tert-butyl [4-(adamantan-1-yl)phenyl]carbamate

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence