benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in ethyl acetate; acetonitrile 3 h;

in isopropyl alcohol T=55 - 65°C; 3.5 h; Large scale reaction;

1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 2: water; lithium hydroxide hydrate / ethanol 3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 4: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 5: isopropyl alcohol / 60 °C View Scheme

1: lithium triethylborohydride / toluene / -70 - -60 °C 2: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 3: water; lithium hydroxide hydrate / ethanol 4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 5: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 6: isopropyl alcohol / 60 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine 2: lithium triethylborohydride / toluene / -70 - -60 °C 3: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 4: water; lithium hydroxide hydrate / ethanol 5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 6: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 7: isopropyl alcohol / 60 °C View Scheme

1: water; lithium hydroxide hydrate / ethanol 2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 3: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 4: isopropyl alcohol / 60 °C View Scheme

1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 2: isopropyl alcohol / 60 °C View Scheme

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 18 h / 20 °C View Scheme