Multi-step reaction with 9 steps
1.1: trifluorormethanesulfonic acid / nitrobenzene / 0 - 20 °C
2.1: triethylamine / dichloromethane / 0 - 20 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -5 °C / Inert atmosphere
4.2: Cooling
5.1: N-benzyl-trimethylammonium hydroxide / toluene; methanol
5.2: 0 - 20 °C
6.1: dichloromethane / 2 h / 20 °C
7.1: water / 1,2-dichloro-ethane / 0.17 h
7.2: 16 h
8.1: hydrogen / palladium on carbon / ethanol / 16 h / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
9.2: 18 h / 20 °C
With
lithium aluminium tetrahydride; trifluorormethanesulfonic acid; water; hydrogen; N-benzyl-trimethylammonium hydroxide; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
palladium on carbon;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; nitrobenzene; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;