Acetone → HCID 58168719, compound

Participants

Reaction Steps

To a mixture of 3,5-difluoro-7-hydroxy adamantane-1-carboxylic acid (1.04 g) and acetone (10 mL) were added triethylamine (1.25 mL) and ethyl chloroformate (860 μL) under ice-cooling, followed by stirring at the same temperature for 30 minutes. To the reaction mixture was added a solution of sodium azide (437 mg) in water (5 mL) under ice-cooling, followed by stirring at the same temperature for 80 minutes. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, water, and saturated brine in this order, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. To the residue were added toluene (12 mL) and 1,4-dioxane (6 mL), followed by stirring at 85° C. for 15 minutes, and then benzyl alcohol (581 mg) and triethylamine (750 μL) were added thereto, followed by stirring at 95° C. for 4 hours. The mixture was cooled to room temperature, and then water was added thereto, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, water, and saturated brine in this order, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain benzyl (3,5-difluoro-7-hydroxyadamantan-1-yl)carbamate (1.15 g) as a white powder.

Provenance & Evidence