pyridine in dichloromethane T=20°C; 5 h;

1: 1.) ozone, 2.) lithium aluminum hydride / 1.) acetonitrile, -15 deg C, 130 min, 2.) THF, 22 deg C, 10 min 2: 2.31 g / pyridine / 1.) 0 deg C, 13 min, 2.) room temperature, 2 h View Scheme

1: sodium tetrahydroborate / methanol; tert-butyl alcohol / 0.5 h / Reflux 2: toluene-4-sulfonic acid / tetrahydrofuran / 4 h / 20 °C 3: pyridine / dichloromethane / 5 h / 20 °C View Scheme

1: 530 mg / sodium hydride / dimethylformamide / 22 °C 2: 156 mg / aq. N hydrochloric acid / methanol / 0.17 h View Scheme