Multi-step reaction with 12 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 0.5 h / -78 °C
2.1: dirhodium tetraacetate / dichloromethane / 0 - 20 °C
3.1: sodium tetrahydroborate; ethanol / 0.5 h / -40 °C
4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C
5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 24 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 17 h / 20 °C
7.1: pyridine; trifluoromethylsulfonic anhydride / tetrahydrofuran / 1.08 h / 0 °C
8.1: hydroxylamine hydrochloride; triethylamine / ethanol; methanol / 17 h / 70 °C
9.1: 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 / 1 h / 20 °C
9.2: 17 h / 90 °C
10.1: lithium hydroxide monohydrate; mercaptoacetic acid / N,N-dimethyl-formamide / 17 h / 30 °C
11.1: triethylamine / dichloromethane / 1 h / 0 °C
12.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
With
pyridine; hydrogenchloride; dirhodium tetraacetate; sodium tetrahydroborate; n-butyllithium; lithium hydroxide monohydrate; ethanol; trifluoromethylsulfonic anhydride; hydroxylamine hydrochloride; ammonium chloride; benzotriazol-1-ol; mercaptoacetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;