Multi-step reaction with 11 steps
1.1: tert-butyl methyl ether; toluene / 20 °C / Heating / reflux
2.1: esperase 8.0L / water; dimethyl sulfoxide / 90 h / 40 °C / pH 8.5 / Heps*Na buffer; Enzymatic reaction; Resolution of racemate
3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
4.1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C
5.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C
6.1: 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
7.1: lithium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C
7.2: pH 4
8.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / Heating / reflux
8.2: 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C
11.1: MgBr2*Et2O / tetrahydrofuran / 0 - 20 °C
11.2: 3 h / -78 - 0 °C
With
4-methyl-morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; esperase 8.0L; 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; 1,4-dioxane; methanol; dichloromethane; tert-butyl methyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;