Multi-step reaction with 8 steps
1: 98 percent / Et3N / CH2Cl2 / Ambient temperature
2: 82 percent / NaH, DMPU / tetrahydrofuran / 1.5 h / Ambient temperature
3: NaBH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 1.5 h
4: imidazole / CH2Cl2 / 1.5 h
5: 81 percent / morpholime, N-iodosuccinamide (NIS) / CH2Cl2 / 3 h / 0 - 20 °C
6: 51 percent / NaH, DMPU / tetrahydrofuran / 1.5 h / Ambient temperature
7: 1.) Zn, 1,2-dibromoethane, 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, 0-5 deg C, 2.) THF, 65 deg C, 5 h
8: 86 percent / NaOMe, MeOH / tetrahydrofuran / 0.33 h
With
morpholine; 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); N-Iodosuccinamide; sodium methylate; sodium hydride; ethylene dibromide; triethylamine; zinc;
In
tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether;
DOI:10.1021/jm970251r