Multi-step reaction with 8 steps
1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 16.5 h / 0 - 20 °C
2: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate; edetate disodium / acetonitrile / 9 h / 0 °C
3: triethylamine / dichloromethane / 3 h / 0 °C
4: sodium azide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 72 h / 60 °C
5: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; 1,4-dioxane / 6 h / 20 °C
6: triethylamine / tetrahydrofuran; water / 2 h / 0 °C
7: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.17 h / 0 °C
8: toluene / 1.5 h / 110 °C
With
hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Oxone; sodium azide; Shi's ketone; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; toluene; acetonitrile;
2: |Shi Asymmetric Epoxidation / 7: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2013.03.022