Multi-step reaction with 10 steps
1.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 18.25 h / 20 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere
3.2: 5 h / -78 - 20 °C / Inert atmosphere
4.1: potassium carbonate / methanol / 1.5 h / 20 °C / Inert atmosphere
5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere
5.2: 1 h / 0 - 20 °C / Inert atmosphere
6.1: N-iodo-succinimide; silver nitrate / acetone / 2 h / 20 °C / Darkness; Inert atmosphere
7.1: pyridine; potassium diazodicarboxylate; acetic acid / methanol / 1 h / Inert atmosphere
8.1: methanol; ammonium chloride; zinc / tetrahydrofuran; water / 1 h / 20 °C / Sonication; Inert atmosphere
9.1: 1H-imidazole / dichloromethane / 10 h / 20 °C / Inert atmosphere
10.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl acetamide / 6 h / 65 °C / 760.05 Torr / Inert atmosphere
With
pyridine; 1H-imidazole; methanol; bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; (-)-N-methylephedrine; potassium diazodicarboxylate; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; silver nitrate; acetic acid; triethylamine; zinc;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; acetone; toluene; mineral oil;
DOI:10.1002/chem.201003489