Multi-step reaction with 9 steps
1: 53 percent / tetrabutylammonium hydrogen sulfate, 5percent aq. NaOH / CH2Cl2 / 24 h / Heating
2: NaH / dimethylformamide / 2 h / 20 °C
3: HCl / methanol / 5 h / 20 °C
4: 95 percent / NaH / dimethylformamide / 2 h / 20 °C
5: (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate / 1,2-dichloro-ethane / 4 h
6: 92 percent / HCl / CH2Cl2; methanol / 1 h / 20 °C
7: 1) 1H-tetrazole, 2) tert-butyl hydroperoxide / 1) CH2Cl2, acetonitrile, 15 min., 2) 0 deg C, 45 min.
8: 82 percent / 2.5percent trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
9: 2) N-methylimidazole / 1) dioxane, 20 deg C, 30 min., 2) 20 deg C, 1 h
With
1-methyl-1H-imidazole; 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; trifluoroacetic acid;
(1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate;
In
methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(92)85037-Z