Multi-step reaction with 7 steps
1: 61 percent / KOAc, Pd(PPh3)4 / N,N-dimethyl-acetamide / 12 h / 150 °C
2: 92 percent / ethanol / 4 h / Heating
3: 1.) NaCNBH3, p-TsOH, 2.) aq. NaOH / 1.) THF, RT, 37 h, 2.) THF, reflux, 3.5 h
4: 52 percent / propan-2-ol / 16 h / 80 °C
5: 93 percent / aq. K2CO3 / methanol / 3 h / Heating
6: 1.) N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride, 1-hydroxybenzotriazole, Et3N / 1.) DMF, 30 min, 2.) DMF, RT, 3 h
7: 100 percent / H2CO2H / 4 h / Ambient temperature
With
sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); formic acid; potassium acetate; sodium cyanoborohydride; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
methanol; ethanol; N,N-dimethyl acetamide; isopropyl alcohol;
DOI:10.1021/jm970873c