Multi-step reaction with 7 steps
1: 91 percent / ethanol; H2O / 20 h
2: 100 percent / acetic anhydride
3: 83 percent / K2CO3 / dimethylformamide / 72 h
4: 80 percent / H2 / 5percent Pd/C / dimethylformamide; ethyl acetate / 3 h / 78 °C / 2327.2 Torr
5: 1) borane-pyridine complex, HCl, 2) Et3N / 1.) EtOH, 0 deg C, 2.) dichloromethane, RT, overnight
6: BuLi / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C
7: 1.) (CF3CO)2O, 2.) BF3*OEt2 / 1.) dichloromethane, -18 deg C, 20 min, 2.) dichloromethane, RT, 1 h
With
hydrogenchloride; n-butyllithium; borane pyridine; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; potassium carbonate; triethylamine; trifluoroacetic anhydride;
palladium on activated charcoal;
In
ethanol; water; ethyl acetate; N,N-dimethyl-formamide;