Multi-step reaction with 12 steps
1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 4 h / 20 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Inert atmosphere
2.2: 18 h / 20 °C / Inert atmosphere
3.1: palladium on activated charcoal; hydrogen / ethanol; water / 3 h / 85 °C / 7500.75 Torr
4.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere; Microwave irradiation
7.1: methanesulfonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere
8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
8.2: 1 h / 20 °C / Inert atmosphere
9.1: hydrogen; citric acid / ethanol; water / 24 h / 60 °C / 45004.5 Torr
10.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
10.2: 20 °C / Inert atmosphere
11.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
12.1: hydrogenchloride; methanol / 20 °C
With
hydrogenchloride; methanol; triethylsilane; sodium tetrahydroborate; methanesulfonic acid; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2012.01.098