Multi-step reaction with 14 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.42 h / 0 °C
1.2: 1.25 h / 10 °C
2.1: pyridinium hydrobromide perbromide / 1,4-dioxane / 1 h / 20 °C
3.1: water
4.1: ammonium chloride; zinc / tetrahydrofuran; water / 3 h
5.1: caesium carbonate / N,N-dimethyl-formamide / 18 h
6.1: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 760.05 Torr
7.1: chloroform / 17 h / Reflux
8.1: hydrogenchloride / methanol
9.1: ethylenediamine; sodium hydroxide / methanol / 0.5 h / pH 10
10.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; methanol; water / 0.27 - 0.28 h / 0 °C
11.1: tetrahydrofuran; methanol; water / 1 h / 65 °C
12.1: sodium hydride / mineral iol; N,N-dimethyl-formamide / 0.25 h
12.2: 1.5 h
13.1: sodium hydroxide / ethanol / 1.5 h / 60 °C
14.1: tributylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C
With
hydrogenchloride; tributylphosphine; di-tert-butyl-diazodicarboxylate; water; hydrogen; pyridinium hydrobromide perbromide; sodium hydride; ammonium chloride; caesium carbonate; ethylenediamine; sodium hydroxide; zinc; sodium nitrite;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; mineral iol; water; N,N-dimethyl-formamide; mineral oil;