Multi-step reaction with 12 steps
1.1: potassium carbonate / acetonitrile
2.1: n-butyllithium / tetrahydrofuran
3.1: palladium on activated charcoal; hydrogen / ethanol / 20 °C / 760.05 Torr
3.2: 0.25 h / 20 °C
3.3: 3 h / Reflux
4.1: nitric acid; acetic acid / 0.5 h / 70 °C
5.1: tin(II) chloride dihdyrate; hydrogenchloride / ethanol / 3 h / 80 °C
6.1: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 13 h / 0 - 20 °C
7.1: chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer / N,N-dimethyl-formamide / 12 h / 20 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
9.1: triethylamine / dichloromethane / 12.5 h / 0 - 20 °C
10.1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C
11.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C
12.1: hydrogenchloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 6 h / 20 °C
With
hydrogenchloride; n-butyllithium; tert.-butylnitrite; tin(II) chloride dihdyrate; chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer; trimethylsilylazide; palladium on activated charcoal; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; nitric acid; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
7.1: |Huisgen Cycloaddition;
DOI:10.1021/jm401536b