Multi-step reaction with 9 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere
1.2: 1 h / 0 - 20 °C
2.1: N,N,N',N'-Tetraethylethylenediamine; n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - -10 °C / Inert atmosphere
2.2: 1 h / -78 - 20 °C
2.3: -10 °C / pH 2 - 3
3.1: methanol / 20 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere
5.1: piperidine / acetic acid / methanol / 18 h / 60 °C
6.1: sodium hydroxide; water / methanol / 18 h / 65 °C
6.2: pH ~ 2 - 3
7.1: triethylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C
7.2: 18 h / 20 °C
8.1: sodium hydroxide; water / methanol / 18 h / Reflux
8.2: pH 2
9.1: triethylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C
9.2: 18 h / 20 °C
With
piperidine; hydrogenchloride; n-butyllithium; N,N,N',N'-Tetraethylethylenediamine; water; sodium hexamethyldisilazane; triethylamine; HATU; sodium hydroxide;
acetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; N,N-dimethyl-formamide;