Multi-step reaction with 8 steps
1.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: dimethyl sulfoxide / 0.75 h / 80 °C / Inert atmosphere
3.1: sodium methylate; hexamethyldisilathiane / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
4.1: ethanol / 0.5 h / Inert atmosphere; Reflux
5.1: sodium hydroxide; water / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
6.1: triethylamine; diphenyl phosphoryl azide / toluene / 2.08 h / 20 - 90 °C / Inert atmosphere
6.2: 1 h / Inert atmosphere; Reflux
7.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 17 h / 0 - 20 °C / Inert atmosphere
8.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
8.2: 16 h / 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; hexamethyldisilathiane; diphenyl phosphoryl azide; water; sodium methylate; benzotriazol-1-ol; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
6.1: Curtius Rearrangement / 6.2: Curtius Rearrangement;