Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / Reflux
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr
3.1: sodium carbonate / methanol / 0.5 h
4.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
4.2: 23.17 h / -78 - 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 0.17 h / 0 - 20 °C
6.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 90 °C
7.1: triphenylphosphine / tetrahydrofuran; water / 2 h / Reflux
8.1: pyridine / dichloromethane / 0.5 h / 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 21 h / 20 °C / 760.05 Torr
10.1: pyridine / dichloromethane / 0.17 h
11.1: potassium carbonate / methanol / 0.17 h / 20 °C
12.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
With
pyridine; n-butyllithium; sodium azide; palladium 10% on activated carbon; hydrogen; sodium carbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.ejmech.2013.03.003