Multi-step reaction with 10 steps
1: dimethyl sulfoxide / 48 h / 120 °C / Inert atmosphere
2: triethylamine / dichloromethane / 0.08 h / Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C
4: acetic acid; palladium 10% on activated carbon; hydrogen / 1,4-dioxane; water / 5 h / 760.05 Torr
5: triethylamine / dichloromethane / 0.08 h / 20 °C
6: diisobutylaluminium hydride / dichloromethane; hexane / 1.33 h / -78 - 20 °C / Inert atmosphere
7: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 19 h / 20 °C / Molecular sieve
8: sodium hydrogensulfite; toluene-4-sulfonic acid / N,N-dimethyl acetamide / 6 h / 155 °C
9: hydrogenchloride / 24 h / Reflux
10: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
With
hydrogenchloride; sodium azide; tetrapropylammonium perruthennate; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; acetic acid; 4-methylmorpholine N-oxide; triethylamine;
In
1,4-dioxane; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;