Multi-step reaction with 15 steps
1: dicyclohexylamine (DCHA) / tetrahydrofuran / 0 °C
2: 70percent perchloric acid / Ambient temperature
3: 100 percent / 1 M KOH / methanol
4: triethylamine / tetrahydrofuran / 1 h / 0 °C
5: sodium borohydride / tetrahydrofuran; H2O / 4 h / Ambient temperature
6: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature
7: 81 percent / Zn, AcOH / 3 h / Irradiation
8: 100 percent / trifluoroacetic acid / 0.5 h / Ambient temperature
9: 54 percent / acetonitrile / 60 °C
10: 30percent HBr / CH2Cl2; acetic acid / 0.17 h
11: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH2Cl2
12: 66 percent / O-benzylhydroxylamine, Pd(PPh3)4 / CH2Cl2 / 5 h
13: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH2Cl2
14: 74 percent / O-benzylhydroxylamine, Pd(PPh3)4 / CH2Cl2 / 5 h
15: 54 percent / 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH2Cl2
With
potassium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); perchloric acid; N-benzyloxyamine; di-isopropyl azodicarboxylate; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; N-cyclohexyl-cyclohexanamine; triphenylphosphine; trifluoroacetic acid; zinc;
In
tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1021/jm00107a013