Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 21 h / 0 - 20 °C / Inert atmosphere
2.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 °C
3.1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / -10 - 20 °C / Inert atmosphere
4.1: 10% palladium on carbon; hydrogen / methanol / 1 h
5.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere
5.2: -20 - 20 °C / Inert atmosphere
6.1: sodium hydroxide / methanol; water / 3 h / 60 °C
6.2: pH 1
7.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere
7.2: -20 - 20 °C / Inert atmosphere
8.1: 10% palladium on carbon; hydrogen / methanol / 3 h
9.1: methanol / 3 h / 20 °C
9.2: 16 h / 20 °C
With
4-methyl-morpholine; hydrogenchloride; 10% palladium on carbon; hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; isobutyl chloroformate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100155