N-(tert-Butoxycarbonyl)-2-aminoacetonitrile

24424-99-5

151-63-3

85363-04-8

The general procedure for the synthesis of 2-(Boc-amino)acetonitrile from di-tert-butyl dicarbonate and aminoacetonitrile sulfate was as follows: first, 3 mmol of aminoacetonitrile sulfate was dissolved in 50 mL of anhydrous methanol at room temperature and protected by nitrogen. Subsequently, 770 mg (4.5 mmol) of L-cysteine methyl ester hydrochloride and 0.63 mL (4.5 mmol) of triethylamine were added to this solution. The reaction mixture was stirred at room temperature for 3 hours, after which the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and washed sequentially with saturated sodium bicarbonate solution and brine. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated, and finally purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 5:1) to afford a methyl ester derivative of the target product 2-(Boc-amino)acetonitrile. Next, 0.9 mL (0.9 mmol) of a 1N lithium hydroxide solution was added to 1.0 mmol of a 5 mL methanol solution of the above methyl ester derivative at 0 °C. The suspension was stirred at room temperature for 1 h. Upon completion of the reaction, it was diluted with 20 mL of acetone to promote precipitation of the product. The white solid was collected by filtration and dried to give purified 2-(Boc-amino)acetonitrile.