Multi-step reaction with 12 steps
1.1: thionyl chloride / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 25 °C
1.2: 3 h / 75 °C
2.1: triethylamine / dichloromethane / 16 h / 0 - 25 °C
3.1: sodium tetrahydroborate / methanol / 0 - 25 °C
4.1: toluene-4-sulfonic acid / chlorobenzene / 140 °C
5.1: potassium osmate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 16 - 24 h / 0 - 25 °C
5.2: 0.5 h / 25 °C
6.1: 1H-imidazole / dichloromethane / 2.5 h / 0 - 25 °C
7.1: 2-iodoxybenzoic acid / tetrahydrofuran; dimethyl sulfoxide / 5 h / 25 °C
8.1: potassium tert-butylate / toluene / 1 h / 0 °C
8.2: 3 h / 0 °C
9.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 - 25 °C
9.2: 2 h / 0 °C
10.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; ethanol; water / 1.5 h / 25 - 60 °C
11.1: hydrogenchloride / 1,4-dioxane; methanol; dichloromethane / 2 h / 25 °C
12.1: pyridine; 4-Nitrophenyl chloroformate / dichloromethane / 2 h / 0 - 25 °C
12.2: 1 h / 0 °C
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; potassium osmate; dimethylsulfide borane complex; 2-iodoxybenzoic acid; potassium tert-butylate; potassium carbonate; toluene-4-sulfonic acid; 4-Nitrophenyl chloroformate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III);
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; chlorobenzene; toluene; tert-butyl alcohol;