1: 92 percent / diisopropylethylamine / 1,2-dichloro-ethane / 3 h / 55 °C 2: 91 percent / NaBH4 / ethanol / 0.5 h / 0 °C 3: 84 percent / imidazole / dimethylformamide / 1 h / 0 °C 4: 92 percent / OsO4; NaIO4 / tetrahydrofuran; H2O 5: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 6: 74 percent / CrO3; H2SO4 / H2O / 0.5 h / 0 °C View Scheme

hydrogenchloride in acetone 1 h; Heating;

1: 87 percent / Zn / dimethylformamide / 0.5 h 2: 84 percent / aq. HCl / acetone / 1 h / Heating View Scheme