Multi-step reaction with 10 steps
1.1: lithium tetrafluoroborate / ethylene glycol / 95 °C / Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 1.08 h / 0 - 20 °C / Inert atmosphere
4.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: dimethyl sulfoxide / 0.75 h / 80 °C / Inert atmosphere
6.1: sodium methylate; hexamethyldisilathiane / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
7.1: ethanol / 0.5 h / Inert atmosphere; Reflux
8.1: sodium hydroxide; water / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
9.1: triethylamine; diphenyl phosphoryl azide / toluene / 2.08 h / 20 - 90 °C / Inert atmosphere
9.2: 1 h / Inert atmosphere; Reflux
10.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 17 h / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; methanol; dmap; sodium tetrahydroborate; lithium tetrafluoroborate; n-butyllithium; hexamethyldisilathiane; diphenyl phosphoryl azide; water; sodium methylate; methanesulfonyl chloride; triethylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
9.1: Curtius Rearrangement / 9.2: Curtius Rearrangement;