Hydrochloric Acid → HCID 18359893, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 95 mg (0.49 mmol) of the above-obtained 7-ethoxycarbonylimidazo[5,1-b]thiazole in 10 ml of tetrahydrofuran (THF) was added 300 mg of lithium borohydride. The mixture was stirred at 80° C. (the oil bath temperature) for one hour, and then cooled. To this reaction solution, 15 ml of methanol was added little by little with ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Concentrated hydrochloric acid was added to this solution little by little with ice-cooling. The resulting mixture was stirred at room temperature for one hour, and concentrated under reduced pressure. To the residue was added a 50% aqueous solution of potassium carbonate to obtain a solution, which was then extracted four times with methylene chloride. The organic layer was dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting with a 3:17 mixture of methanol and ethyl acetate to give 30 mg (yield 40%) of 7-hydroxymethylimidazo[5,1-b]thiazole.

Provenance & Evidence