Multi-step reaction with 10 steps
1: magnesium sulfate; p-toluenesulfonic acid monohydrate / CH2Cl2 / 0 - 20 °C
2: 100 percent / HCl / dioxane / 1 h / 20 °C
3: 76 percent / HATU; ethyldiisopropylamine / CH2Cl2 / 18 h / 0 - 20 °C
4: 100 percent / HCl / dioxane; ethyl acetate / 20 °C
5: HATU; ethyldiisopropylamine / CH2Cl2 / 0 - 20 °C
6: 100 percent / hydrogen / palladium on carbon / ethyl acetate; ethanol / 16 h / 20 °C
7: 72 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphane / CH2Cl2 / 24 h / 20 °C
8: lithium hydroxide / tetrahydrofuran; methanol; H2O / 0 - 20 °C
9: 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; EDC; N-methylmorpholine / dimethylformamide; CH2Cl2 / -20 - -10 °C
10: 41 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
With
4-methyl-morpholine; hydrogenchloride; lithium hydroxide; hydrogen; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1,1'-azodicarbonyl-dipiperidine;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
7: Mitsunobu reaction;
DOI:10.1002/anie.200501553