1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-60°C; 1.75 h; 2: With triethylamine in dichloromethane T=-60 - 0°C; 1.5 h;

2,6-dimethylpyridine; 5 palladium on charcoal; hydrogen in toluene T=20 - 35°C; P=2585.81 Torr; Inert atmosphere;

hydrogenchloride in tetrahydrofuran; water T=11 - 20°C; 3.16667 h;

1.1: 96 percent / CuSO4 / 3 h / 95 °C 2.1: hydrogen / nanostructurated Ru(trioctylamine) supported on γ-Al2O3 / tetrahydrofuran / 24 h / 80 °C / 15200 Torr 2.2: conc. HCl / 24 h / Heating 3.1: HCl / 4 h / 20 °C View Scheme

1.1: hydrogen / nanostructurated Ru(trioctylamine) supported on γ-Al2O3 / tetrahydrofuran / 24 h / 80 °C / 15200 Torr 1.2: conc. HCl / 24 h / Heating 2.1: HCl / 4 h / 20 °C View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 - 20 °C 1.2: 1 h / 0 - 25 °C 2.1: Dess-Martin periodane / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme