Multi-step reaction with 10 steps
1: 92 percent / LiOH, H2O / tetrahydrofuran; methanol
2: 86 percent / EDCI, HOBt / CH2Cl2 / 12 h / 25 °C
3: 70 percent / CBr4, Ph3P / diethyl ether / 12 h / 25 °C
4: NaH / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) -78 deg C, 12 h
5: 0.5 N aq. HCl / tetrahydrofuran / 14 h / 25 °C
6: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C
7: H2 / Pd-C / tetrahydrofuran / 3 h / 25 °C
8: NaHCO3 / tetrahydrofuran / 25 °C
9: 90 percent / n-Bu4NF / dimethylformamide / 4 h / 25 °C
10: 3.0 M HCl / ethyl acetate / 0.5 h / 25 °C
With
hydrogenchloride; lithium hydroxide; carbon tetrabromide; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93447-1