Multi-step reaction with 12 steps
1: sodium; propan-1-ol / toluene / 12 h / Reflux; Inert atmosphere
2: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
4: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
7: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
8: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
9: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 3 h / 0 - 20 °C / Inert atmosphere
10: hydrogenchloride / methanol; 1,4-dioxane / 3 h / 20 °C / Inert atmosphere
11: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
12: 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol; copper(II) sulfate; sodium L-ascorbate / tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere
With
hydrogenchloride; propan-1-ol; phosphorus pentachloride; palladium 10% on activated carbon; hydrogen; sodium; sodium tris(acetoxy)borohydride; sodium carbonate; benzotriazol-1-ol; copper(II) sulfate; acetic acid; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol;
In
tetrahydrofuran; 1,4-dioxane; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/ml400370w