Multi-step reaction with 8 steps
1: 72 percent / HCl / dioxane / 60 °C
2: 94 percent / methanol; tetrahydrofuran / -60 - 10 °C
3: dicyclohexylcarbodiimide, hydroxybenzotriazole / 1.) THF 2.) Et3N
4: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C
5: 87 percent / LiAlH4 / tetrahydrofuran / -78 - 20 °C
6: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch2Cl2
7: 84 percent / NaIO4, KMnO4, Na2CO3, CH2N2 / dioxane; H2O; diethyl ether
8: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H2O / 175 °C
With
diazomethane; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; sodium periodate; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; sodium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; dimethyl sulfoxide;
DOI:10.1039/c39870000267