Potassium tert-butoxide → HCID 66958691, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, potassium tert-butoxide (142.7 mL of a 1 M solution in THF) was added to a solution of tert-butyl 3-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (57.2 g, 118.9 mmol) in THF (142.7 mL). After the reaction was stirred at ambient temperature for ten minutes, additional potassium tert-butoxide (32 mL of a 1 M solution in THF) was added. The reaction was stirred overnight at ambient temperature and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 67-minute gradient from 0:100 to 3:97) and recrystallized sequentially from dichloromethane and acetonitrile to provide 26.99 g of tert-butyl 3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Provenance & Evidence