Multi-step reaction with 10 steps
1.1: ammonium bicarbonate / water / 18 h / 25 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 14 h / 25 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C / Inert atmosphere
3.2: 3 h / -78 - 25 °C / Inert atmosphere
4.1: hydrogenchloride / water / 2 h / 25 °C / Inert atmosphere
5.1: caesium carbonate / N,N-dimethyl-formamide / 14.5 h / 0 - 25 °C / Inert atmosphere
6.1: sodium tetrahydroborate / methanol / 3 h / 0 - 25 °C / Inert atmosphere
7.1: thionyl chloride / 3 h / 25 °C / Inert atmosphere
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 25 °C / Inert atmosphere
8.2: 72 h / 25 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 20 h / 25 °C / 760.05 Torr
10.1: caesium carbonate / N,N-dimethyl-formamide / 8.5 h / 25 °C / Inert atmosphere
With
hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; ammonium bicarbonate; caesium carbonate; triethylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201201467