Multi-step reaction with 7 steps
1: MgSO4, molecular sieves / cyclohexane; benzene / 2.5 h / Ambient temperature
2: Et3N, molecular sieves, MgSO4 / cyclohexane; benzene / 3 h / Ambient temperature
3: 11 percent / di-isopropylcyclohexylamine, 1.4M n-BuLi, hexamethylphosphoramide (HMPA) / 0.5 h / -75 °C
4: 1.) osmium-tetroxide (OsO4); 2.) NaIO4 / dioxane; H2O / 1.) RT, 15 min; 2.) 15 deg C, 15 min
5: NaH / 1,2-dimethoxy-ethane / 1 h
6: H2 / 10percent Pd/C / ethanol
7: 1.) CF3COOH; 2.) NaHCO3 / 1.) CH2Cl2, RT; 2.) H2O, pH=7.0
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; osmium(VIII) oxide; n-butyllithium; molecular sieve; hydrogen; sodium hydrogencarbonate; magnesium sulfate; diisopropyl(cyclohexyl)amine; triethylamine; trifluoroacetic acid;
palladium on activated charcoal; sodium hydride;
In
1,4-dioxane; 1,2-dimethoxyethane; ethanol; cyclohexane; water; benzene;
DOI:10.1248/cpb.37.315