Dichloromethane → HCID 66823227, compound

Participants

Reaction Steps

A 1M solution of diisobutylaluminium hydride (3.53 ml, 3.53 mmol) in toluene was added dropwise to a solution of 1-methyl-1H-imidazole-4-sulfonic acid {2-[3-(benzyl-cyanomethyl)-4-fluoro-phenoxy]-ethyl}-amide (721 mg, 1.683 mmol) in 4 ml dichloromethane at 0° C. The reaction was stirred at this temperature for 30 min and then added to a suspension of sodium borohydride (2546 mg, 67.3 mmol) in 5 ml tetrahydrofuran/methanol (1:3) at 0° C., stirred for 1 h allowing to warm up to room temperature. 1 N sodium hydroxide solution was added and the mixture was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated to obtain the free amine as a white solid which was purified by flash chromatography on SiO2 cartridge (10% methanol in dichloromethane) to obtain 285 mg (36%) product as a colourless solid.

Provenance & Evidence