pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane T=20°C; 18 h;

1: 83 percent / NaBH4 / ethanol / 12 h / 25 °C 2: pyridine / 48 h / 25 °C View Scheme

1.1: sodium hydroxide / water / 0.08 h / 20 °C 1.2: 72 h 2.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C 3.1: pyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 18 h / 20 °C View Scheme

1.1: sodium hydroxide / water / 0.08 h / 20 °C 1.2: 72 h 2.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C 3.1: pyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 18 h / 20 °C View Scheme