Multi-step reaction with 8 steps
1: 4-methylmorpholine / CH2Cl2 / 0.33 h / 0 °C
2: CH2Cl2 / 1.) 0 deg C, 20 min, 2.) RT, 2 h
3: diisobutylaluminum hydride / toluene / 4 h / -78 °C
4: 1.) NaN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 2 h, b) from -78 deg C to 0 deg C, 10 min
5: 98 percent / aq. NaOH / ethanol / 3 h / 23 °C
6: 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH2Cl2 / 23 °C
7: HCl / dioxane / 2 h / 23 °C
8: 4-methylmorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 23 °C
With
4-methyl-morpholine; hydrogenchloride; dmap; sodium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
1,4-dioxane; ethanol; dichloromethane; toluene;
DOI:10.1021/jm980068d