Multi-step reaction with 9 steps
1: potassium carbonate / methanol / Reflux; Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
4: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 80 °C / Inert atmosphere
5: potassium hydroxide / tetrahydrofuran; methanol; water / Reflux; Inert atmosphere
6: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 20 °C / 760.05 Torr / Inert atmosphere
7: pyridine / 0 °C / Inert atmosphere
8: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / Inert atmosphere
9: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 8 h / Inert atmosphere
With
pyridine; dmap; copper(l) iodide; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; L-proline; potassium hydroxide; diisopropyl-carbodiimide;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm300178u