Multi-step reaction with 13 steps
1: triphenylphosphine; di-isopropyl azodicarboxylate / 2 h / 60 °C
2: hydrogen; palladium(II) hydroxide / acetic acid; ethanol / 120 h / 20 °C / 1?atm
3: trifluoroacetic acid / dichloromethane / 0.67 h / 0 - 20 °C
4: Rh/Al2O3; trifluoroacetic acid; hydrogen / acetic acid; ethanol / 20 °C / 10?atm
5: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C
6: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 °C
7: sodium hydride / N,N-dimethyl-formamide; ethanol / 0.67 h / 0 °C
8: potassium carbonate / water / 0.5 h / 70 °C
9: hydrogen; palladium(II) hydroxide / acetic acid; ethanol / 20 °C / 1?atm
10: trichloroisocyanuric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0.5 h / 0 - 20 °C
11: sodium tris(acetoxy)borohydride / tetrahydrofuran / 2.5 h / 20 °C
12: hydrogenchloride; water / 1,4-dioxane / 3 h
13: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 72 h
With
hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; di-isopropyl azodicarboxylate; trichloroisocyanuric acid; Rh/Al2O3; water; hydrogen; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003