Multi-step reaction with 16 steps
1: 87 percent / potassium fluoride/celite / acetonitrile / 12 h / 85 °C
2: 92 percent / H2, aq. NaOH / Raney Ni / ethanol / 12 h / 2327.2 Torr
3: magnesium sulfate / methanol / 4 h / Ambient temperature
4: NaBH4 / methanol / Ambient temperature
5: 96 percent / KF/celite / acetonitrile / 12 h / 85 °C
6: 87 percent / H2, aq. NaOH / Raney Ni / ethanol / 12 h / 2327.2 Torr
7: magnesium sulfate / methanol / 4 h / Ambient temperature
8: NaBH4 / methanol / Ambient temperature
9: 85 percent / potassium fluoride/celite / acetonitrile / 12 h / 85 °C
10: 79 percent / H2, aq. NaOH / Raney Ni / ethanol / 12 h / 2327.2 Torr
11: magnesium sulfate / methanol / 4 h / Ambient temperature
12: NaBH4 / methanol / Ambient temperature
13: trifluoroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature
14: 60 percent / 2-methoxy-ethanol / 12 h / 80 °C
15: 88 percent / pyridine, triethylamine / 12 h / Ambient temperature
16: 74 percent / triphenyl phosphine, diethyl azodicarboxylate / dioxane / 10 h / Ambient temperature
With
pyridine; potassium fluoride; sodium hydroxide; sodium tetrahydroborate; Celite; hydrogen; magnesium sulfate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate;
nickel;
In
1,4-dioxane; methanol; ethanol; dichloromethane; 2-methoxy-ethanol; acetonitrile;
DOI:10.1002/jhet.5570300532