Multi-step reaction with 9 steps
1.1: lithium hydroxide; water / tetrahydrofuran / 16 h / 20 °C
1.2: pH 4
2.1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C
4.1: tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride / dichloromethane / 0.25 h / Heating / reflux
5.1: lithium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C
5.2: pH 4
6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / Heating / reflux
6.2: 4 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C
9.1: MgBr2*Et2O / tetrahydrofuran / 3 h / 0 °C / Cooling with acetone-dry ice
With
4-methyl-morpholine; 1H-imidazole; lithium hydroxide; MgBr2*Et2O; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; HATU; 1,1'-carbonyldiimidazole;
tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;