Multi-step reaction with 9 steps
1: oxalyl chloride, N,N-dimethylformamide / CH2Cl2 / 1 h
2: triethylamine / CH2Cl2
3: 90 percent / conc. sulfuric acid / diethyl ether / 3 h
4: 1.) N-methylmorpholine N-oxide, osmium tetraoxide, 2.) sodium periodate / 1.) THF, H2O, overnight, 2.) ethanol, H2O, 2 h
5: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s); H2O / 0.5 h
6: 73 percent / 1-hydroxybenzotriazole, triethylamine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide / dimethylformamide
7: 83 percent / nitromethane, aluminum chloride / benzene / 1 h
8: 32 percent / sodium hypophosphite monohydrate, pyridine, acetic acid / Raney nickel / H2O / 2 h / 60 °C
9: sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; tetrahydrofuran; various solvent(s); H2O / 0.5 h
With
pyridine; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; sodium hypophosphite; aluminium trichloride; sodium dihydrogen phosphate; oxalyl dichloride; nitromethane; sulfuric acid; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide;
nickel;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/jm00001a014