Multi-step reaction with 11 steps
1.1: dmap; triethylamine / ethyl acetate / 6 h / 0 - 20 °C
2.1: nitric acid; acetic anhydride / acetic acid / 5 h / -10 - 20 °C
3.1: methanol; sodium methylate / 5 h / 20 °C
4.1: ammonium chloride / ethanol / Reflux; Inert atmosphere
5.1: sodium tetrahydroborate / ethanol / 12 h / Reflux
5.2: 0 - 20 °C
6.1: boron trioxide; acetic acid / 14 h / 20 - 70 °C / Inert atmosphere
7.1: sulfuric acid; periodic acid / water / 0 - 20 °C
7.2: pH 3.8 - 3.9
8.1: acetic acid / ethanol / 20 - 40 °C
8.2: 2 h / 20 °C
9.1: triethylamine / methanol / 2 h / 20 °C
10.1: sodium hydride / 2 h / 70 °C
11.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
11.2: SunFire.(TM). Prep Cl 8 OBD.(TM).
With
hydrogenchloride; methanol; dmap; boron trioxide; sodium tetrahydroborate; sulfuric acid; nitric acid; sodium methylate; acetic anhydride; sodium hydride; ammonium chloride; acetic acid; periodic acid; triethylamine;
In
1,4-dioxane; methanol; ethanol; water; acetic acid; ethyl acetate;