Multi-step reaction with 8 steps
1: Et3N / CH2Cl2 / 0.5 h
2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h
3: 65.8 percent / aq. FeCl3, carbon, H2NNH2 / methanol / 6 h / 70 °C
4: 81.9 percent / AcOH / 4 h / 100 °C
5: 2.) DMF / 1.) CH2Cl2, a) -20 deg C, 30 min, b) RT, 1 h, 2.) CH2Cl2, a) -78 deg C, 30 min, b) RT, 1 h
6: 52.2 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 0 - 20 °C
7: HOBt, WSCD*HCl / dimethylformamide / 2.5 h / 0 - 20 °C
8: 78.8 percent / 1 N aq. NaOH / ethanol / 1 h / 60 °C
With
sodium hydroxide; lithium aluminium tetrahydride; WSCD*HCl; iron(III) chloride; sodium hydride; pyrographite; benzotriazol-1-ol; acetic acid; triethylamine; N,N-dimethyl-formamide; hydrazine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm980330i