Multi-step reaction with 11 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.83 h / -75 - -65 °C
1.2: 1.25 h / -70 - -65 °C
1.3: -60 - -10 °C / pH 1 - 2
2.1: potassium permanganate / water; tert-butyl alcohol / 2.92 h / 30 - 65 °C
2.2: 0.17 h / 20 °C
2.3: 15 - 25 °C / pH 1
3.1: sulfuric acid / Reflux
4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere
5.1: lithium hexamethyldisilazane / tetrahydrofuran / 19 h / 0 - 20 °C
5.2: 1 h / 20 °C
6.1: N-Bromosuccinimide / dichloromethane / 2.25 h / -5 - 20 °C
6.2: 20 °C
7.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.17 h / 135 °C
8.1: sulfuric acid / ethanol / 20 °C / Reflux
9.1: pyridine / dichloromethane / 20 °C
9.2: 20 °C
9.3: 2 h / 60 °C
10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C
11.1: 1-methyl-pyrrolidin-2-one / 2 h / 100 °C
With
pyridine; 2,2,6,6-tetramethyl-piperidine; 1-methyl-pyrrolidin-2-one; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium permanganate; N-Bromosuccinimide; n-butyllithium; sulfuric acid; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane;
bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; tert-butyl alcohol;