Multi-step reaction with 9 steps
1: 1.) ozone, 2.) Me2S / 1.) GH2Cl2, -78 deg C, 2.) CH2Cl2, RT, overnight
2: sodium borohydride / methanol / 3 h / 0 °C
3: 86 percent / triethylamine / CH2Cl2 / 6 h / Ambient temperature
4: 1.) sodium hydride / 1.) DMF, RT, 30 min, 2.) DMF, RT, 14 h
5: 4N HCl / dioxane; methanol / 1 h / Ambient temperature
6: N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / 14 h / Ambient temperature
7: 4N HCl / dioxane / 1 h / Ambient temperature
8: N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / Ambient temperature
9: CH2Cl2 / 1 h / Ambient temperature
With
4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; sodium hydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00097a010