Multi-step reaction with 7 steps
1: hydrogen; palladium 10% on activated carbon / N,N-dimethyl-formamide; methanol / 1 h / 20 °C
2: dmap; diethyl cyanophosphonate; triethylamine / N,N-dimethyl-formamide; tetrahydrofuran / 8 h / 0 - 20 °C / Inert atmosphere
3: hydrogen; palladium 10% on activated carbon / methanol / 0.75 h
4: triethylamine / N,N-dimethyl-formamide / 8.5 h / 0 - 20 °C / Inert atmosphere
5: potassium carbonate / N,N-dimethyl-formamide; acetone / 8 h / Inert atmosphere; Reflux
6: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C / Inert atmosphere
7: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
With
dmap; diethyl cyanophosphonate; palladium 10% on activated carbon; hydrogen; potassium carbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2013.05.126