Multi-step reaction with 14 steps
1.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C / Inert atmosphere
2.1: triethylamine; triflic azide; zinc(II) sulfate / water; dichloromethane; methanol / 2.5 h / 0 - 20 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane; methanol; 2,2,2-trifluoroethanol / 72 h / 0 - 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide; dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere
5.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / tetrahydrofuran / 3 h / -65 °C / Inert atmosphere
5.2: 1 h / -60 - 20 °C / Inert atmosphere
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.33 h / -50 °C / Inert atmosphere
6.2: 29 h / -25 °C / Inert atmosphere
7.1: trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 80 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.42 h / 0 °C / Inert atmosphere
8.2: 48 h / 20 °C / Inert atmosphere
9.1: bis(dibenzylideneacetone)-palladium(0); morpholine / dichloromethane / 4 h / 20 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide; dichloromethane / 24 h / 20 °C / Inert atmosphere
11.1: triphenylphosphine; 2,6-dimethylpyridine / 7 h / 60 °C / Inert atmosphere
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / 8 h / -70 - 20 °C / Inert atmosphere
13.1: triethylamine; 2,6-dimethylpyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
With
morpholine; 2,6-dimethylpyridine; hydrogenchloride; Bromotrichloromethane; triflic azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) sulfate; trimethyltin(IV) hydroxide; sodium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2,2,2-trifluoroethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201600994