Multi-step reaction with 9 steps
1: NaBH4 / methanol / 0 °C
2: 1.) H2, 2.) pyridine / 1.) Pd/C / 1.) MeOH, 50 deg C, 2.) CH2Cl2
3: dicyclohexylcarbodi-imide, Me2SO, pyridine, CF3COOH / benzene / 0 - 25 °C
4: CH2Cl2 / 25 °C
5: H2 / (Ph3P)3RhCl / benzene / 50 °C
6: H2 / 10percent Pd/C / methanol / 0 °C
7: 2,2'-dipyridyl disulphide, PPh3
8: 47 percent / 1.) LiN(SiMe3)2, 2.) Ph2PO-O-NH2 / tetrahydrofuran / 1.) -78 deg C
9: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CH2Cl2
With
pyridine; sodium tetrahydroborate; 2,2'-dipyridyldisulphide; O-(diphenylphosphinyl)hydroxylamine; hydrogen; dimethyl sulfoxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane;
palladium on activated charcoal; Wilkinson's catalyst;
In
tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1039/c39850000194