Multi-step reaction with 12 steps
1: acetone / 1.5 h / 55 °C
2: hydrogenchloride / ethyl acetate; water / 1.5 h / 55 °C
3: sodium hydrogencarbonate; iodine; potassium iodide / water / 5 h / 20 °C
4: sodium hydroxide / water
5: ammonium hydroxide / water; ethanol / 45 °C
6: ammonium hydroxide / ethanol / 20 °C / Cooling with ice
7: triethylamine / dichloromethane / 2.5 h / 0 °C / Inert atmosphere
8: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 48 h / 75 °C
9: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C
10: sodium hydrogencarbonate / ethyl acetate; water / 0 - 20 °C
11: sodium ethanolate; water / ethanol / 15 h / 20 - 45 °C / Inert atmosphere
12: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; ammonium hydroxide; sodium azide; 15-crown-5; palladium 10% on activated carbon; water; hydrogen; iodine; sodium ethanolate; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium iodide; sodium hydroxide;
In
ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2017.01.021