sodium tetrahydroborate in methanol T=20°C; 2 h;

1.1: Na2[PdCl4]; sodium acetate; acetic acid / 72 h / 20 °C 1.2: 1 h / 20 °C 1.3: 20 h / -78 - 20 °C 2.1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C 3.1: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 4.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 5.1: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C 2: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 3: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 4: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 3: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 2: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C 3.1: pyridine; hydroxylamine hydrochloride / 4 h / 80 °C 4.1: Na2[PdCl4]; sodium acetate; acetic acid / 72 h / 20 °C 4.2: 1 h / 20 °C 4.3: 20 h / -78 - 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C 6.1: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 7.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 8.1: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / 4 h / 80 °C 3.1: Na2[PdCl4]; sodium acetate; acetic acid / 72 h / 20 °C 3.2: 1 h / 20 °C 3.3: 20 h / -78 - 20 °C 4.1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C 5.1: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 6.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 7.1: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme

1.1: pyridine; hydroxylamine hydrochloride / 4 h / 80 °C 2.1: Na2[PdCl4]; sodium acetate; acetic acid / 72 h / 20 °C 2.2: 1 h / 20 °C 2.3: 20 h / -78 - 20 °C 3.1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C 4.1: hydrogenchloride; titanium(III) chloride; ammonium acetate / tetrahydrofuran; water / 6 h / 20 °C 5.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 760.05 Torr 6.1: sodium tetrahydroborate / methanol / 2 h / 20 °C View Scheme