Multi-step reaction with 9 steps
1: 1.) NaH / 1.) DMF, 45 min, 2.) DMF, 25 deg C, 14 h
2: 100 percent / 1 N HCl / methanol / 24 h / 25 °C
3: 92 percent / pyridine / tetrahydrofuran / 14 h / 25 °C
4: 71 percent / pyridine / CH2Cl2 / 14 h / 25 °C
5: 70 percent / dimethylformamide / 16 h / 80 °C
6: 100 percent / NaBH4 / ethanol / 1 h / 55 °C
7: pyridine / 14 h / 25 °C
8: p-toluenesulfonic acid / CH2Cl2; methanol / 1 h / 25 °C
9: 1.) POCl3, Et3N / 1.) THF, 0 deg C, 45 min, 2.) THF, 25 deg C, 14 h
With
pyridine; hydrogenchloride; sodium tetrahydroborate; sodium hydride; toluene-4-sulfonic acid; triethylamine; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00050a009