Multi-step reaction with 8 steps
1: 1.) KN(TMS)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, a) -78 deg C, 3 h, b) from -78 deg C to RT, 4 h
2: 100 percent / 1 N aq.NAOH / methanol / 16 h / Heating
3: OsO4, NaIO4 / tetrahydrofuran; ethyl acetate / 24 h
4: NaHCO3 / H2O; ethanol / 12 h / Ambient temperature
5: 41 percent / 2-chloro-1-methylpyridinium iodide, Et3N / CH2Cl2 / 8 h / Heating
6: 100 percent / NH3 / methanol / 0.75 h / Ambient temperature
7: 4 N HCl / dioxane / 18 h / Ambient temperature
8: HOBt*H2O, Et3N, EDC*HCl / dimethylformamide / 96 h
With
hydrogenchloride; sodium hydroxide; sodium periodate; osmium(VIII) oxide; 2-chloro-1-methyl-pyridinium iodide; ammonia; potassium hexamethylsilazane; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm990140n