Multi-step reaction with 12 steps
1: sodium dithionite; water / benzene / 0.08 h
2: potassium carbonate / N,N-dimethyl-formamide / 120 h
3: potassium carbonate / N,N-dimethyl-formamide / 22 h / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Cooling with ice
5: Dess-Martin periodane / dichloromethane / 1.1 h / Cooling with ice
6: ammonium acetate / 13 h / 120 °C
7: sodium tetrahydroborate / methanol; dichloromethane / 0.25 h / Cooling with ice
8: phenyl isocyanate; triethylamine / benzene / 40 h / 45 - 50 °C
9: hydrogen; boric acid / tetrahydrofuran; methanol; water / 21 h
10: 1H-imidazole; triethylamine / dichloromethane / 21 h / Inert atmosphere; Darkness
11: selenium(IV) oxide; water; triethylamine / tetrahydrofuran / 3 h / 50 - 60 °C
12: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h
With
1H-imidazole; selenium(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium dithionite; palladium 10% on activated carbon; ammonium acetate; water; hydrogen; boric acid; potassium carbonate; Dess-Martin periodane; phenyl isocyanate; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo200399z