Water → HCID 89525502, compound

Participants

Reaction Conditions

Reaction Steps

304 mg (8 mmol, 2 eq) of lithium aluminum hydride were added to a solution of 968 mg (4 mmol, 1 eq) of 2-[azido(tetrahydrothiopyran-4-yl)methyl]-5-methylfuran in 10 ml of tetrahydrofuran cooled to −10° C. The reaction medium was stirred at ambient temperature for 2 hours. The reaction medium was cooled to 0° C. and water with a solution of sodium hydroxide at 2 N and diethyl ether were added (precipitation of the aluminum and lithium salts). The reaction medium was filtered through celite and then the filtrate was treated with a 3 N hydrochloric acid solution. The aqueous phase was recovered and basified with a 15 N sodium hydroxide solution and then extracted with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated. 728 mg of C-(5-methylfuran-2-yl)-C-(tetrahydrothiopyran-4-yl)methylamine were obtained. Yield=86%.

Provenance & Evidence