Triethylamine → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide

Participants

Reaction Steps

According to the general method outlined above for the synthesis of Intermediates 8, triethylamine (1.94 ml, 13.94 mmol) was slowly added to a suspension of (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)-2-pyrrolidinecarbonitrile (3.71 g, 11.62 mmol) and hydroxylamine.hydrochloride (0.97 g, 13.94 mmol) in ethanol (150 ml), under stirring. The reaction mixture was allowed to stir at 80° C. for 16 h, and then cooled to ambient temperatures. The solvent was removed by evaporation and the solid was suspended in water (100 ml) then filtered. The solid was washed with diethyl ether (2×100 ml) whilst on the sinter and then dried in vacuo at 40° C., to give the desired product, (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (3.35 g, 82%).

Provenance & Evidence