Multi-step reaction with 10 steps
1.1: triphenylphosphine; diethylazodicarboxylate / toluene; benzene / 2 h / 0 - 20 °C / Inert atmosphere
2.1: methanol; ammonia / water / 3 h / 0 - 20 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
4.1: sodium hydroxide / tetrahydrofuran; methanol; water / 2 h / 0 - 20 °C
4.2: pH 3 - 4
5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere
6.1: water; acetic acid / tetrahydrofuran / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere
10.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; dmap; tetrabutyl ammonium fluoride; ammonia; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene;
DOI:10.1016/j.tet.2011.08.014