Multi-step reaction with 11 steps
1: 1) oxalyl chloride, DMSO, 2) NET3 / 1) CH2Cl2, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C
2: 91 percent / benzene / 0.17 h / 25 °C
3: 1) Ac2O, conc. H2SO4, 2) NaOMe / 1) 0 deg C, 10 min, 2a) MeOH, 0 deg c, 10 min, 2b) 25 deg C, 0.5h
4: 100 percent / H2NNH2*HCl, pyridine / 3 h / 25 °C
5: 75 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C
6: 28 percent / H2, HOAc / Raney-Ni-W4 / H2O; dioxane / 4 h / 25 °C / 760 Torr
7: 65 percent / NEt3 / CH2Cl2 / 48 h / 25 °C
8: 80 percent / BH3*Me2S / tetrahydrofuran / 0.5 h / 0 °C
9: 39 percent / imidazole / dimethylformamide / 4 h / 0 °C
10: 60 percent / imidazole / dimethylformamide / 0 °C
11: 95 percent / pyridine / 12 h / 25 °C
With
pyridine; 1H-imidazole; sodium hypochlorite; oxalyl dichloride; hydrazine hydrochloride; dimethylsulfide borane complex; sulfuric acid; hydrogen; sodium methylate; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine;
Raney-Ni-W4;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/0008-6215(91)89017-A