Multi-step reaction with 7 steps
1: 2.) H2 / 2.) 5percent Pd/C / 1.) water, EtOH, 40 deg C, 4 h, 2.) water, EtOH, 60 psi, 16 h
2: 1.) n-BuLi / 1.) hexane, THF, 4 h, 2.) hexane, THF, 25 deg C, 20 h
3: 77 percent / HOAc, 48percent aq. HBr / 24 h / Heating
4: triethylamine / CH2Cl2 / 16 h
5: 1.) NaOEt, 2.) NaI / 1.) EtOH, 0.25 h, 0 deg C, 2.) EtOH, RT, 48 h
6: NH4OH / ethanol / 4 h
7: 86 percent / H2O / 24 h / Heating
With
ammonium hydroxide; n-butyllithium; hydrogen bromide; hydrogen; sodium ethanolate; acetic acid; triethylamine; sodium iodide;
palladium on activated charcoal;
In
ethanol; dichloromethane; water;
DOI:10.1021/jm00388a028