Multi-step reaction with 10 steps
1: AgClO4, Ag2CO3, molecular sieve / CH2Cl2 / 24 h / Ambient temperature
2: Na/EtOH / CH2Cl2 / 0.5 h / Ambient temperature
3: 90 percent / H2, quinoline / 5percent Pd-BaSO4 / methanol / 20 h / 760 Torr / Ambient temperature
4: 87 percent / Et3N / dioxane; H2O / 16 h
5: pyridine
6: 60 percent / NaN3 / hexamethylphosphoric acid triamide / 15 h / 80 °C
7: 95 percent / Na/EtOH / CH2Cl2 / 0.5 h / Ambient temperature
8: 96 percent / pyridine
9: 74 percent / NaI, NaBH3CN / hexamethylphosphoric acid triamide / 16 h / 70 - 75 °C
10: 76 percent / H2, quinoline / 5percent Pd-BaSO4 / hexamethylphosphoric acid triamide / 12 h / Ambient temperature
With
quinoline; sodium azide; molecular sieve; ethanol; hydrogen; silver perchlorate; sodium; sodium cyanoborohydride; triethylamine; silver carbonate; sodium iodide;
palladium on barium sulfate;
In
1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1016/0008-6215(82)84035-4