Multi-step reaction with 12 steps
1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 60 °C
3: sodium tetrahydroborate / ethanol / 2 h / 20 °C
4: phosphorus tribromide / diethyl ether / 1.5 h / 0 °C
5: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -50 - 0 °C
6: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C
7: borane-THF / tetrahydrofuran / 0 °C
8: manganese(IV) oxide / dichloromethane / 20 °C
9: hydroxylamine hydrochloride; pyridine / ethanol / 20 °C
10: palladium 10% on activated carbon; hydrogenchloride; hydrogen / water; ethanol / 3 h / 20 °C / 3000.3 - 3750.38 Torr
11: diethyl cyanophosphonate; triethylamine / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
12: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 3.5 h / 0 °C / Inert atmosphere
With
pyridine; hydrogenchloride; manganese(IV) oxide; sodium tetrahydroborate; borane-THF; lithium hydroxide monohydrate; diethyl cyanophosphonate; palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; phosphorus tribromide; potassium carbonate; potassium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2013.02.003