Multi-step reaction with 10 steps
1: phenyl isocyanate, triethylamine / benzene / 12 h / Ambient temperature
2: 100 percent / Dowex-50W / methanol / 2 h / Ambient temperature
3: 1.) sodium periodate, 2.) sodium borohydride / 1.) MeOH, H2O, RT, 15 min, 2.) MeOH, 0 deg C, 30 min
4: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 1 h, 2.) RT, 4 h
5: 80 percent / acetic acid, H2 / Raney nickel / methanol; H2O / 1.5 h
6: 85 percent / zink triflate / CH2Cl2 / 0.25 h / Ambient temperature
7: 79 percent / aq. HCl / 0.25 h / Ambient temperature
8: 75 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C
9: 4-(dimethylamino)pyridine / dimethylformamide / 12 h / 70 - 80 °C
10: 90 percent / H2 / 10percent Pd/C / methanol / 24 h
With
hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; Dowex-50W; hydrogen; tetra-(n-butyl)ammonium iodide; L-Selectride; zinc trifluoromethanesulfonate; sodium hydride; phenyl isocyanate; acetic acid; triethylamine;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00206a010