Multi-step reaction with 12 steps
1.1: sodium carbonate / water / 1 h
2.1: sodium hydride / diethyl ether / 1 h / 20 °C
3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 - 60 °C
4.1: hydrogen; acetic acid / palladium 10% on activated carbon / ethanol / 60 °C / 2585.81 Torr
5.1: potassium carbonate / tetrahydrofuran / 20 °C
6.1: sodium ethanolate / ethanol / 4 h / Heating / reflux
7.1: methanol; potassium hydroxide; water / Heating / reflux
7.2: pH ~ 2
8.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 80 °C
8.2: 20 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0 - 20 °C
10.1: hydrogenchloride; methanol / 1,4-dioxane / 1 h / 20 °C
11.1: sodium tris(acetoxy)borohydride / water; 1,2-dichloro-ethane / 2 h
12.1: ethanol; n-heptane
With
hydrogenchloride; methanol; potassium hydroxide; diphenyl phosphoryl azide; water; hydrogen; sodium ethanolate; sodium tris(acetoxy)borohydride; sodium hydride; sodium carbonate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; n-heptane; dichloromethane; water; 1,2-dichloro-ethane; toluene;