Multi-step reaction with 6 steps
1: 73.4 percent / H2 / 10percent Pd/C / acetic acid / 41 h / Ambient temperature
2: 79 percent / pyridine / 24 h / Ambient temperature
3: 1.) BF3*Et2O, AcOH, Ac2O, 2.) p-TsOH*H2O / 1.) reflux, 18.5 h, 2.) reflux, 20 h
4: 100 percent / LiOH*H2O / tetrahydrofuran; H2O / 4 h / Ambient temperature
5: 1.) N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 4 h, 2.) acetone, DMF, reflux, 18 h
6: 50.8 percent / K2CO3 / acetone; dimethylformamide / 2 h / Heating
With
pyridine; dmap; lithium hydroxide; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00128a028