Multi-step reaction with 10 steps
1.1: copper(I) bromide dimethylsulfide complex; methylmagnesium bromide / tetrahydrofuran; dimethylsulfide; dibutyl ether / 0 - 20 °C / Inert atmosphere
2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 - 0 °C / Inert atmosphere
3.1: sodium azide / dimethyl sulfoxide / 45 h / 20 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / Inert atmosphere
5.1: lithium hydroxide / tetrahydrofuran; water / 1 h / 0 °C / Inert atmosphere
6.1: caesium carbonate / methanol; water / pH 8 / Inert atmosphere
6.2: 1 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / ethyl acetate / 1 h / 20 °C / Inert atmosphere
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole / tetrahydrofuran; dichloromethane / 20 °C / Inert atmosphere
9.1: hydrogenchloride / ethyl acetate / 20 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran; dichloromethane / 20 °C / Inert atmosphere
With
hydrogenchloride; sodium azide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; methylmagnesium bromide; water; hydrogen; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; HATU; lithium hydroxide;
In
tetrahydrofuran; methanol; dimethylsulfide; dichloromethane; dibutyl ether; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jm2007062