Multi-step reaction with 8 steps
1.1: toluene-4-sulfonic acid; copper(II) sulfate / acetone / 24 h / 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen; citric acid / methanol / 48 h / 20 °C / 760.05 Torr
3.1: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C / Inert atmosphere
4.1: barium hydroxide octahydrate / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere
5.1: 1H-imidazole / methanol; N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere
6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
6.2: 12 h / 20 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr
8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / Inert atmosphere
With
1H-imidazole; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; citric acid;
In
tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.201200103