Multi-step reaction with 7 steps
1: 77 percent / 2N NaOH / H2O; tetrahydrofuran
2: 74 percent / diisopropylethylamine, 1-hydroxybenzotriazole monohydrate, DCC / CH2Cl2 / 1.) 0 deg C, 0.5 h; 2.) room temperature 1.5 h.
3: 46 percent / NH3 / methanol / 1.) 0 deg C; 2.) room temperature 5 days
4: 1.) H2, 2.) HOBt (monohydrate), DCC / Pd-black / 1.) EtOH, 3 h; 2.) DMF, room temperature, 3h.
5: 1.) diethylamine, 2.) HOBt / 1.) DMF, 2 h, 2.) DMF, 3 h.
6: 1.) HNEt2, 2.) DCC, HOBt / 1.) DMF, 2 h, room temperature; 2.) DMF, 2 h, room temperature.
7: 1.) NHEt2; 2.) HOBt / 1.) DMF, 2 h, room temperature; 2.) DMF, 2 h, room temperature.
With
sodium hydroxide; ammonia; hydrogen; benzotriazol-1-ol; 1-hydroxybenzotriazol-hydrate; diethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide;
palladium;
In
tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo01289a016