Multi-step reaction with 12 steps
1.1: nitric acid; sulfuric acid / 6 h / -5 - 20 °C
2.1: N,N-dimethyl-formamide / 5 h / 120 °C
3.1: hydrogen / palladium 10% on activated carbon / ethanol / 20 °C
4.1: sodium hydroxide / 3 h / 60 °C
5.1: tert-butyl alcohol / 16 h / 50 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
6.2: 20 °C
7.1: sulfuric acid / 2 h / 50 °C
8.1: tert-butyl alcohol / 10 h / 50 °C
9.1: lithium hexamethyldisilazane; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 1 h / -78 °C
9.2: 0.33 h / -20 °C
10.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
11.1: 4-methyl-morpholine / dichloromethane / 1.5 h / 0 °C
12.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -78 °C
12.2: pH 2 - 3 / Cooling with ice
With
4-methyl-morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; hydrogen; nitric acid; trifluoroacetic acid; sodium hydroxide; lithium hexamethyldisilazane;
palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;