Multi-step reaction with 7 steps
1: 94 percent / triethylamine / 4-(dimethylamino)pyridine / dimethylformamide / 8.5 h / 40 °C
2: 65 percent / 1N NaOH / methanol / 5 h / Ambient temperature
3: 1.) triethylamine / 1.) ether, -15 deg C, 30 min then 0 deg C, 15 min, 2.) 0 deg C, 2.5 h
4: 64 percent / silver benzoate, triethylamine / methanol / 2 h / Ambient temperature
5: 1N KOH / methanol / 23 h / Ambient temperature
6: 92 percent / hydrogen / Pd-C / methanol / 1 h
7: 2.) hydrogen / 2.) Pd-C / 1.) ethanol, r.t., 45 min, 2.) ethanol, r.t., 20 h then 40 deg C, 4 h
With
potassium hydroxide; sodium hydroxide; hydrogen; silver benzoate; triethylamine;
dmap; palladium on activated charcoal;
In
methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.34.2732