Multi-step reaction with 9 steps
1: triflic azide; potassium carbonate; copper(II) sulfate / methanol; dichloromethane; water / 12 h / 0 - 20 °C
2: triethylamine / toluene / 21 h / 50 - 55 °C
3: sodium hydride / N,N-dimethyl-formamide; toluene / 18 h / 50 - 60 °C
4: hydrogenchloride / methanol; water; toluene / 20 h / 50 - 60 °C
5: Dimethyldisulphide; trifluoromethylsulfonic anhydride / tetrahydrofuran / 0.33 h / -10 °C / Molecular sieve
6: lithium aluminium tetrahydride / tetrahydrofuran / 1.17 h / 0 - 20 °C
7: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 12 h / 20 °C
8: hydrogen; palladium(II) hydroxide / methanol; dichloromethane / 12 h / 20 °C
9: pyridine / 16 h / 0 - 20 °C
With
4-methyl-morpholine; pyridine; hydrogenchloride; lithium aluminium tetrahydride; Dimethyldisulphide; trifluoromethylsulfonic anhydride; triflic azide; hydrogen; palladium(II) hydroxide; sodium hydride; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; copper(II) sulfate; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/cbic.201200004