Multi-step reaction with 11 steps
1.1: acetic anhydride; acetic acid / 1.5 h / 120 °C
1.2: 1 h / Cooling with ice
2.1: triethylamine; trichlorophosphate / 2 h / 0 - 120 °C
3.1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C
4.1: dimethyl sulfoxide / 3 h / 135 °C
4.2: pH 3 - 4
5.1: sulfuric acid / 4 h / 20 °C
5.2: 0 °C / Reflux
5.3: 0 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 10 - 20 °C / Inert atmosphere
6.2: 0.33 h / 0 - 20 °C
7.1: manganese(IV) oxide / tetrahydrofuran / 20 °C / Inert atmosphere
8.1: piperidine / acetic acid / methanol / 18 h / 60 °C / Inert atmosphere
9.1: sodium hydroxide; water / methanol / 18 h / 65 °C
9.2: pH 3 - 4
10.1: triethylamine; HATU / N,N-dimethyl-formamide / 20 h / 20 °C
11.1: sodium hydroxide; water / methanol / 20 °C
11.2: pH 3 - 4
With
piperidine; manganese(IV) oxide; lithium aluminium tetrahydride; sulfuric acid; water; acetic anhydride; acetic acid; triethylamine; HATU; sodium hydroxide; trichlorophosphate;
acetic acid;
In
tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;