Aluminium lithium hydride → HCID 57657257, compound

Participants

Reaction Steps

A round bottom flask, equipped with a stir bar, was charged with ethyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate (1.0 g, 2.4 mmol) and anhydrous tetrahydrofuran (20 mL). The reaction mixture was cooled in an ice bath. Lithium aluminum hydride (92 mg, 2.4 mmol) was added in one portion. After 2 hours additional lithium aluminum hydride (92 mg, 2.4 mmol) was added in one portion. The ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. The reaction was quenched by successive dropwise addition of water (1 mL), 10% sodium hydroxide solution (1 mL) and water (3 mL). The reaction mixture was maintained at ambient temperature for 18 hours and then diluted with diethyl ether and water. The fractions were separated and the aqueous fraction was extracted with diethyl ether (3×25 mL). All of the organic fractions were combined and then concentrated to dryness under reduced pressure. Purification by chromatography using a HORIZON HPFC system (silica cartridge, 0-20% CMA/chloroform) provided 0.8 g of 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propan-1-ol as a white crystalline solid, mp 177-178° C.

Provenance & Evidence