Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / dichloromethane; mineral oil / -78 °C
1.2: 20 °C
2.1: ammonium carbonate / water / Reflux
3.1: sodium hydroxide / ethylene glycol / 38 h / 120 °C
4.1: triethylamine / dichloromethane / 0 °C / Reflux
5.1: sodium hydroxide / methanol / 4 h / 20 °C
6.1: lithium hydroxide / water / 60 h / 37 °C / pH 8.5
7.1: hydrogenchloride; water / Reflux
8.1: water; acetone / 2 h / 20 °C
9.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 8 h / 75 °C / Inert atmosphere
10.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / -5 °C
11.1: sodium tetrahydroborate; acetic acid / dichloromethane / 3.5 h / -5 °C / Inert atmosphere
12.1: toluene / 3 h / Reflux
With
hydrogenchloride; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); water; ammonium carbonate; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; sodium hydroxide; lithium hydroxide;
In
1,4-dioxane; methanol; dichloromethane; water; ethylene glycol; acetone; toluene; mineral oil;