Multi-step reaction with 16 steps
1: 80percent oily NaH / dimethylformamide / Ambient temperature
2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature
3: NaBH4 / methanol / 1 h / Ambient temperature
4: pyridine / Ambient temperature
5: 1M aq. NaOH / methanol / 7 h / Heating
6: KHCO3 / dioxane; H2O / Ambient temperature
7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature
8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature
9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C
10: 1M aq. NaOH / dioxane / 15 h / Heating
11: KHCO3 / dioxane; H2O / Ambient temperature
12: 100 percent / pyridine / 4 h / Ambient temperature
13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature
14: 91 percent / NaOMe / methanol / 3.5 h / Ambient temperature
15: 83 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature
16: 11 percent / benzylamine / 17 h / 50 °C
With
dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium methylate; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; benzylamine;
In
1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)89338-8