Multi-step reaction with 9 steps
1: 60 percent / NaNH2 / tetrahydrofuran / 4.5 h
2: 97.5 percent / H2 / 5percent Pd/C / ethyl acetate / 4 h / 2327.2 Torr / Ambient temperature
3: 1) glacial acetic acid, conc. HCl, NaNO2, 2) KI, I2 / 1) H2O, 40 min, 0 deg C, 2) overnight, r.t.
4: 88 percent / KOH / aq. ethanol / Heating
5: 98 percent / BH3-THF / tetrahydrofuran / 20 h / Ambient temperature
6: 71 percent / pyridine / Ambient temperature
7: 1) K / 1) benzene, 1 h, reflux, 2) overnight, reflux
8: 66 percent / 1 N HClO4 / dioxane / 10 h / 80 - 100 °C
9: 42 percent / pyridine / diethyl ether / 1) 10 min, 0 deg C, 2) 4.5 h, reflux
With
pyridine; hydrogenchloride; potassium hydroxide; perchloric acid; borane-THF; hydrogen; iodine; sodium amide; acetic acid; potassium iodide; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; ethyl acetate;
DOI:10.1021/jm00129a020