[(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester → (S)-2-(1-Aminoethyl)-1-phenyl-1H-benzo[D]imidazole-6-carbonitrile

Participants

Reaction Steps

A solution of [(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.97 mmol) in TFA (3 mL) was stirred at RT for 30 min. Volatiles were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product was further purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording 2-((S)-1-Aminoethyl)-3-phenyl-3H-benzoimidazole-5-carbonitrile as white crystalline solid (415 mg, 80% over two steps). LCMS: RT 1.99 min [M+H]+ 263.2

Provenance & Evidence