Multi-step reaction with 10 steps
1.1: zinc; ammonium chloride / tetrahydrofuran; methanol / 2 h / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 72 h / 20 °C
3.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 5.75 h / -78 - 20 °C
3.2: 0.5 h / 20 °C / Cooling with ice
4.1: ammonium acetate; acetic acid / 95 °C
5.1: 140 °C
6.1: zinc; ammonium chloride / tetrahydrofuran; methanol / Inert atmosphere
7.1: hydrogenchloride / toluene; 1,4-dioxane / 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon / xylene / 120 °C
9.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C
9.3: pH 5
10.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 4-methyl-morpholine; ammonium chloride / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
With
4-methyl-morpholine; hydrogenchloride; lithium hydroxide monohydrate; ammonium acetate; water; diisobutylaluminium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; xylene;