Multi-step reaction with 12 steps
1.1: sodium nitrite; tetrafluoroboric acid / water / 0.67 h / 0 °C
1.2: 0.5 h / 50 - 130 °C
2.1: sodium hydroxide; water / ethanol / 1 h / 20 °C
2.2: pH ~ 7
3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
4.1: N-chloro-succinimide; potassium tert-butylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
5.1: triethylamine / dmap / tetrahydrofuran / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
7.1: triphenylphosphine; diamide / tetrahydrofuran / 20 °C
8.1: hydrogenchloride; hydrogen / 5%-palladium/activated carbon / ethanol; water; methanol / 1.17 h / 20 °C / Inert atmosphere
9.1: isopropyl alcohol / Reflux
10.1: hydrogen / CM-101 / tetrahydrofuran; methanol / 20 °C
11.1: hydrogenchloride; triethylamine; hydrogen / ethanol; water / 0.33 h / 20 °C
11.3: 72 h / 20 °C
12.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C
With
1H-imidazole; hydrogenchloride; N-chloro-succinimide; tetrafluoroboric acid; diamide; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; triethylamine; triphenylphosphine; sodium hydroxide; sodium nitrite;
dmap; 5%-palladium/activated carbon;
In
tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;