Triphenylphosphine → HCID 86612262, compound

Participants

Reaction Steps

Triphenylphosphine (6.67 g, 25.5 mmol), tert-butyl N-(tert-butoxycarbonyloxy)carbamate (5.94 g, 25.5 mmol), and diisopropyl azodicarboxylate (5.00 mL, 25.5 mmol) were added to a solution of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (6.56 g, 23.2 mmol) in DMF (100 mL). The reaction mixture was stirred overnight at room temperature, then was concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to provide 9.5 g of N-[(tert-butoxycarbonyl)oxy]-2,2-dimethyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]propanamide, which was used without purification in the next step.

Provenance & Evidence