Multi-step reaction with 11 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 10 - 35 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Cooling with ice
2.2: 1.5 h / 10 - 35 °C
3.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 3 h / 10 - 35 °C
4.1: potassium carbonate / methanol / 2 h / 10 - 35 °C
5.1: N,N,N',N'-tetramethylguanidine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 10 - 35 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 - 35 °C
7.1: potassium tert-butylate / tetrahydrofuran / 10 - 35 °C
8.1: toluene; tetrahydrofuran / 1 h / 0 °C / Cooling with ice
9.1: ethanol; sodium tetrahydroborate / 1 h / 0 °C / Cooling with ice
10.1: triethylamine / tetrahydrofuran / 1 h / 10 - 35 °C
11.1: sodium azide / N,N-dimethyl-formamide / 60 °C
With
1H-imidazole; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; ethanol; potassium tert-butylate; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; potassium carbonate; triethylamine; N,N,N',N'-tetramethylguanidine;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;