Multi-step reaction with 10 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 18 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
3.1: methanol / pyridinium p-toluenesulfonate / 12 h / 20 °C
4.1: triethylamine / copper diacetate / dichloromethane; water / 12 h / 20 °C / 4 ? Molecular sieve
5.1: hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux
6.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
8.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 37 - 40 °C
8.2: 3 h / -78 - 20 °C
9.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 0 - 20 °C
9.2: pH 2
10.1: hydrogen / palladium 10% on activated carbon / ethanol / 0.5 h / 2068.65 Torr
With
hydrogenchloride; methanol; chloro-trimethyl-silane; water; hydrogen; potassium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; zinc;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; copper diacetate; pyridinium p-toluenesulfonate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water;