Multi-step reaction with 9 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / 760.05 Torr / Inert atmosphere
1.2: -78 - 20 °C / 760.05 Torr / Inert atmosphere
1.3: 760.05 Torr / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 25 °C / 760.05 Torr / Inert atmosphere
3.1: tetrahydrofuran / 4.5 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere
4.1: toluene / 18 h / 760.05 Torr / Inert atmosphere; Reflux
5.1: potassium carbonate / methanol / 2 h / 760.05 Torr / Inert atmosphere; Reflux
6.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 760.05 Torr / Inert atmosphere; Reflux
7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 22 °C / 760.05 Torr / Inert atmosphere
8.1: platinum(IV) oxide; hydrogen; hydrogenchloride / 1,4-dioxane; ethyl acetate / 11 h / 25 °C / 760.05 Torr / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / 760.05 Torr / Inert atmosphere
9.2: 0 - 20 °C / 760.05 Torr / Inert atmosphere
With
hydrogenchloride; platinum(IV) oxide; N-Bromosuccinimide; sodium azide; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; lithium hexamethyldisilazane; dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;