Multi-step reaction with 12 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 20 °C
3: dmap; triethylamine / toluene / 16 h / 0 - 20 °C
4: hydrogenchloride; water / ethanol / 24 h / 20 °C
5: pyrrolidine; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine / acetonitrile / 7 h / 0 - 20 °C
6: triphenylphosphine / toluene / 3 h / 20 °C
7: copper(I) trifluoromethanesulfonate benzene / benzene / 3 h / 80 °C
8: pyridine hydrogenfluoride / tetrahydrofuran / 3 h / 20 °C
9: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C
10: palladium on carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C / 760.05 Torr / Darkness
11: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C
12: palladium on carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr
With
pyrrolidine; 4-methyl-morpholine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); copper(I) trifluoromethanesulfonate benzene; palladium on carbon; water; hydrogen; benzotriazol-1-ol; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1002/ejoc.201100034