Dess-Martin periodane in dichloromethane T=20°C;

1: 3 g / NaBH4 / ethanol / Ambient temperature 2: 8.98 g / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / Ambient temperature View Scheme

4-pyrrolidin-1-ylpyridine; triethylamine in dichloromethane Ambient temperature;

1: 30 percent / p-toluenesulfonic acid / benzene / 3.5 h / Heating 2: 1 M MeONa / 1.) methanol, -78 deg C, 10 min, 2.) -78 deg C, 2 h 3: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 4: 76 percent / MnO2 / ethyl acetate / Ambient temperature 5: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 0.5 h, 2.) room temperature, 2 h 6: 50 percent / LiOH, water / 1,2-dimethoxy-ethane / 3 h / Ambient temperature View Scheme

1: 36 percent / p-toluenesulfonic acid / benzene / 3.5 h / Heating 2: 1 M MeONa / 1.) methanol, -78 deg C, 10 min, 2.) -78 deg C, 2 h 3: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 4: 74 percent / MnO2 / ethyl acetate / Ambient temperature 5: 91 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 0.5 h, 2.) room temperature, 2 h View Scheme