Multi-step reaction with 10 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 35 h / 80 - 120 °C
2.1: sodium hydroxide / ethanol; water / 4 h / 20 °C
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 50 °C
3.2: 0.5 h / Cooling with ice
4.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C
5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 3000.3 Torr
6.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 - 120 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8.1: sodium hydroxide; water / ethanol / 3 h / 20 °C
9.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1-methyl-pyrrolidin-2-one / 6 h / 20 - 100 °C
10.1: methylamine / ethanol; water; tetrahydrofuran / 1.5 h
With
1H-imidazole; 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 1,1'-carbonyldiimidazole; methylamine; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; ethyl acetate; N,N-dimethyl-formamide;