Multi-step reaction with 10 steps
1: 75 percent / H2 / Pd/C / methanol
2: 61 percent / KOH, H2O / 1.25 h / Heating
3: 87 percent / H2SO4
4: 38 percent / acetic acid; tetrahydrofuran / 168 h / 20 °C
5: Et3N / CH2Cl2 / 3 h / 20 °C
6: NaCl / dimethylformamide / 0.08 h / Heating
7: conc. HCl / 1 h / 80 °C
8: Et3N / acetone / 0.25 h / 0 °C
9: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg, 30 min, 2.) reflux, 10 min
10: 74 percent / methanol / 24 h / 20 °C
With
hydrogenchloride; potassium hydroxide; sodium azide; sulfuric acid; water; hydrogen; triethylamine; sodium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00166a015