Multi-step reaction with 8 steps
1: 1,3-dicyclohexylcarbodiimide; pyridine; CF3COOH / dimethylsulfoxide / 7 h
2: dimethylsulfoxide
3: 88 percent / potassium azodicarboxylate / pyridine; acetic acid / 4 h
4: 81 percent / pyridine-2-aldoxime; 1,1,3,3-tetramethylguanidine / dioxane; H2O; CHCl3 / 7 h
5: 98 percent / 2-chloro-5,5-dimethyl-2-oxo-2λ5-1,3,2-dioxaphosphinane; 4-methoxy-pyridine 1-oxide; pyridine / 3 h
6: 82 percent / pyridine-2-aldoxime; 1,1,3,3-tetramethylguanidine / dioxane; H2O; CHCl3 / 6.5 h
7: triethylamine trishydrofluoride / tetrahydrofuran / 48 h
8: AgNO3 / tetrahydrofuran; dimethylformamide
With
pyridine; 4-methoxypyridine N-oxide; 2-hydroxyiminomethyl-pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; triethylamine trishydrofluoride; potassium diazodicarboxylate; silver nitrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine;
In
tetrahydrofuran; 1,4-dioxane; pyridine; chloroform; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
1: Oxidation / 2: Condensation / 3: Reduction / 4: Hydrolysis / 5: Condensation / 6: Hydrolysis / 7: Desilylation / 8: Etherification;
DOI:10.1039/a906066i