Multi-step reaction with 10 steps
1: sulfuric acid / 20 h / Reflux
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h
3: tetrahydrofuran / 2 h / -78 - 20 °C
4: tetra-n-butylammonium tribromide / dichloromethane; methanol / 3 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
6: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol / 5 h / 3361.55 Torr
7: triethylamine / dichloromethane / 1 h / 0 - 20 °C
8: acetic acid / 4 h / Reflux
9: potassium carbonate / acetone / 20 °C
10: pyrrolidine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
With
pyrrolidine; hydrogenchloride; dmap; copper(l) iodide; sodium azide; tetra-n-butylammonium tribromide; sulfuric acid; hydrogen; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
platinum(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;