Multi-step reaction with 10 steps
1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2.5 h / -78 °C
1.2: 1.5 h / -78 °C
2.1: hydrazine hydrate / 1,2-dimethoxyethane / 20 - 75 °C
3.1: iodine; potassium hydroxide / 1,4-dioxane / 4 h / 75 °C
4.1: potassium hydroxide / N,N-dimethyl-formamide / 2.5 h / 20 °C
5.1: butan-1-ol / 20 - 190 °C / Microwave irradiation
6.1: tetra-(n-butyl)ammonium iodide; triethylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; N,N-dimethyl-formamide / 70 °C
7.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 0 °C
8.2: 0.58 h / 50 °C
9.1: trifluoroacetic acid / 20 - 70 °C
10.1: triphenylphosphine / carbon tetrabromide; acetonitrile / 2 h / 20 °C / Microwave irradiation
10.2: 0.5 h / 100 °C / Microwave irradiation
With
lithium aluminium tetrahydride; n-butyllithium; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; hydrazine hydrate; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic acid; potassium hydroxide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; carbon tetrabromide; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;