Multi-step reaction with 10 steps
1.1: potassium carbonate / tetrahydrofuran / 72 h / 20 °C
2.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 5.75 h / -78 - 20 °C
2.2: 0.5 h / 20 °C / Cooling with ice
3.1: ammonium acetate; acetic acid / 4.5 h / 90 °C
4.1: tetrahydrofuran / 16 h / 125 °C
5.1: zinc; ammonium chloride / tetrahydrofuran; methanol / 4.5 h / 20 °C
6.1: hydrogenchloride / toluene; 1,4-dioxane / 16 h / 20 °C
6.2: pH 10
6.3: 4.5 h / 125 °C
7.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1.5 h / 20 °C
7.2: pH 4 - 5
8.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 4-methyl-morpholine; ammonium chloride / N,N-dimethyl-formamide / 1.5 h / 20 °C
9.1: hydrogen / palladium on activated charcoal / tetrahydrofuran; methanol / 1.5 h / 20 °C
10.1: acetic acid; sodium tris(acetoxy)borohydride / 1,1-dichloroethane; tetrahydrofuran / 16 h / 20 °C
With
4-methyl-morpholine; hydrogenchloride; lithium hydroxide monohydrate; ammonium acetate; water; hydrogen; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,1-dichloroethane; dichloromethane; N,N-dimethyl-formamide; toluene;