Multi-step reaction with 7 steps
1.1: hydrogenchloride / 1,4-dioxane / 1.5 h / 25 - 40 °C / Inert atmosphere
2.1: sodium acetate / methanol; dichloromethane / 0.5 h / 25 °C / Inert atmosphere
2.2: 2 h / Inert atmosphere
2.3: 0.25 h / Inert atmosphere
3.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 16 h
5.1: N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate / methanol; chloroform / 16 h / 60 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
6.2: 1 h / 25 °C / Inert atmosphere
6.3: 18 h / 60 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 1 h / 25 °C
With
hydrogenchloride; dmap; n-butyllithium; palladium 10% on activated carbon; hydrogen; sodium acetate; N,N,N-trimethylbenzenemethanaminium dichloroiodate; N-ethyl-N,N-diisopropylamine; calcium carbonate;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jm300069y