Multi-step reaction with 8 steps
1.1: dmap; triethylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere
2.1: tetrahydrofuran / -78 - 20 °C / Inert atmosphere
3.1: dmap; 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -60 °C / Inert atmosphere
4.2: 1 h / -60 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 12 h / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 20 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
8.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmcl.2012.09.072