Multi-step reaction with 10 steps
1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C
2.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere
3.1: isopropyl alcohol / 30 - 55 °C
4.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5
4.2: 4 h / 25 - 55 °C / Inert atmosphere
4.3: -70 - -10 °C / Inert atmosphere
5.1: thionyl chloride / 5 h / 40 - 45 °C
6.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere
8.1: chloroform / 0.75 h / -45 - -35 °C
9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 6 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
10.1: ethyl acetate / 0.5 h / Reflux
With
dmap; thionyl chloride; water; hydrogen; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide;
5%-palladium/activated carbon; palladium 10% on activated carbon;
In
tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol; acetonitrile;