Multi-step reaction with 9 steps
1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Cooling with ice
2: copper(l) iodide; piperidine; bis-triphenylphosphine-palladium(II) chloride / toluene / 6 h / 35 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -78 °C
4: sodium hydrogencarbonate / N,N-dimethyl-formamide; ethyl acetate / 20 °C
5: sodium tetrahydroborate / methanol; tetrahydrofuran / 1.5 h / 0 - 20 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
7: ammonium hydroxide / 1,4-dioxane / 12 h / 35 °C
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C
9: water; hydrogenchloride / 1,4-dioxane / 1.17 h / 0 - 20 °C
With
piperidine; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; sodium tetrahydroborate; copper(l) iodide; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;