Multi-step reaction with 12 steps
1.1: tetra-N-butylammonium tribromide / ethanol / 48 h / 20 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / 20 °C
3.1: sodium hydroxide; water / ethanol / 36 h / Reflux
3.2: 0.25 h / pH Ca.5 - Ca.7
4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 1.5 h / 20 °C
5.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C
6.1: toluene / 1 h / 90 °C
7.1: tert.-butyl lithium / tetrahydrofuran / 0 h / -78 - 0 °C
8.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / Reflux; Inert atmosphere
9.1: hydroxylamine hydrochloride / water; ethanol / 1 h / 50 °C
10.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1.5 h / 50 °C
10.2: 18 h / 20 °C
11.1: hydrogenchloride / methanol / 6 h / 65 °C
12.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
12.2: 18 h / 20 °C
With
hydrogenchloride; N-chloro-succinimide; sodium azide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; palladium 10% on activated carbon; hydroxylamine hydrochloride; water; tert.-butyl lithium; ammonium formate; tetra-N-butylammonium tribromide; potassium hexamethylsilazane; 1,1'-carbonyldiimidazole; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;