Multi-step reaction with 11 steps
1.1: sulfuric acid; water; acetic acid / 1.5 h / Reflux
2.1: trichlorophosphate / 5 h / Reflux
2.2: Cooling with ice
3.1: n-butyllithium / tetrahydrofuran; hexanes / -78 °C
3.2: 20 °C / Cooling
3.3: 0.08 h
4.1: sodium azide / water; acetone / 16 h / 70 °C
5.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 17 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.3 h
7.1: ammonium chloride; zinc / tetrahydrofuran; methanol / 1 h
8.1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 60 °C
9.1: hydrogenchloride; water / acetonitrile / 2 h / 60 °C
10.1: sodium tris(acetoxy)borohydride / dichloromethane / 15 h
10.2: 0.75 h
11.1: hydrogen / palladium 10% on activated carbon / 17 h
With
hydrogenchloride; n-butyllithium; sodium azide; lithium hydroxide monohydrate; sulfuric acid; water; hydrogen; sodium tris(acetoxy)borohydride; ammonium chloride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; trichlorophosphate;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;