Multi-step reaction with 12 steps
1: sulfuric acid; water / 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 / methanol; dichloromethane / 3 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 0 - 20 °C
6: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol; water / 5 h / 2068.65 - 3361.55 Torr
7: acetic acid / 4 h / Reflux
8: potassium carbonate / acetone / 1 h
9: pyrrolidine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
10: hydrogen / platinum(IV) oxide / methanol / 36 h / 3361.55 Torr / Inert atmosphere
11: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran
12: trifluoroacetic acid / dichloromethane / 20 °C
With
pyrrolidine; hydrogenchloride; dmap; sodium azide; di-isopropyl azodicarboxylate; sulfuric acid; water; hydrogen; tetra-N-butylammonium tribromide; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid;
platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;