Multi-step reaction with 12 steps
1.1: N,N-dimethyl-formamide / 5 h / 65 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 0 °C
2.2: 0 - 20 °C
3.1: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 3 h / 20 °C / 3040.2 Torr / Inert atmosphere
4.1: tetrahydrofuran / 2 h / Inert atmosphere; Reflux
5.1: sodium hydroxide / ethanol / 5 h / Reflux
5.2: 20 °C / pH 4
6.1: pyridine / 0 - 20 °C / Inert atmosphere
7.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
9.1: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
10.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / 2280.15 Torr
11.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h / 20 °C
With
pyridine; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
2.2: |Wittig Olefination / 9.1: |Wittig Olefination;
DOI:10.1016/j.bmc.2013.02.048