1: 65 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 59 percent / NaNH2 / tetrahydrofuran / 1.5 h / 5 - 22 °C 3: 66 percent / H2, (η6-PhCO2Me)Cr(CO)3 / acetone / 2 h / 120 - 125 °C / 60800 Torr 4: NaBH4 / ethanol; H2O / Ambient temperature 5: aq. KOH / 0.5 h / Ambient temperature 6: 1.) 2,2'-dipyridyl disulfide, PPh3, 2.) AgClO4 / 1.) CH3CN, from 20 deg C to 25 deg C, 2 h, 2.) CH3CN, p-xylene, reflux, 6 h View Scheme

1: 60 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h / 0 °C 2: 62.9 percent / piperidine / 0.22 h / microwave irradiation View Scheme

1: 20.0 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 2: NaBr / dimethylformamide / 2 h / 65 °C View Scheme