Multi-step reaction with 8 steps
1: 90 percent / KOH, tetrabutylammonium bromide / tetrahydrofuran / 1.5 h / Ambient temperature
2: 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) EtOAc, 70 deg C, 2.) benzene, reflux
3: 81.4 percent / benzene / 4 h / Heating
4: 94 percent / NaBH4, AlCl3 / tetrahydrofuran / 0.75 h / Heating
5: tetrahydrofuran / 0 °C
6: aq. NH4OH / tetrahydrofuran / Ambient temperature
7: 96.7 percent / H2 / 10percent Pd/C / ethyl acetate
8: 74.5 percent / K2CO3, KI / dimethylformamide / 5 h
With
potassium hydroxide; ammonium hydroxide; sodium tetrahydroborate; aluminium trichloride; tetrabutylammomium bromide; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm960395q