Multi-step reaction with 11 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C
1.2: 1 h / -78 °C
2.1: hydrogen; quinoline / Lindlars catalyst / ethyl acetate / 0.67 h
3.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere
3.2: 0.17 h
3.3: 24 h / 0 °C
4.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr
4.2: 0 °C
4.3: 0.5 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: sodium hydrogencarbonate / dichloromethane; water / 0.08 h / 0 °C
6.2: 1.5 h / 0 - 20 °C
7.1: ethyl acetate; tetrahydrofuran / Inert atmosphere
7.2: 2 h / 70 °C
7.3: 80 °C
8.1: di-isopropyl azodicarboxylate / dichloromethane / 0 - 20 °C / Inert atmosphere
9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 16 h / 20 °C
9.2: pH 5
10.1: triethylamine / tetrahydrofuran / 0.5 h / -10 °C
11.1: hydrazine hydrate / N,N-dimethyl-formamide / 20 °C
With
quinoline; hydrogenchloride; n-butyllithium; di-isopropyl azodicarboxylate; water; hydrogen; diethylzinc; sodium hydrogencarbonate; hydrazine hydrate; triethylamine; sodium hydroxide;
palladium(II) hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;