1: With diisobutylaluminium hydride in dichloromethane T=-90 - -70°C; 1 h; 2: With hydrogenchloride in dichloromethane; water T=-70 - 20°C;

SPAC

sodium tetrahydroborate in methanol T=0°C; 0.25 h;

1: 90 percent / H2, quinoline / Pd/BaSO4 2: 95 percent / PPh3, Br2 / 3 h / Ambient temperature 3: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 4: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 5: I2 / diethyl ether / 4 h / Ambient temperature 6: NaBH4 / methanol / 0.25 h / 0 °C View Scheme

1: 95 percent / PPh3, Br2 / 3 h / Ambient temperature 2: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 3: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 4: I2 / diethyl ether / 4 h / Ambient temperature 5: NaBH4 / methanol / 0.25 h / 0 °C View Scheme

1: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 2: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 3: I2 / diethyl ether / 4 h / Ambient temperature 4: NaBH4 / methanol / 0.25 h / 0 °C View Scheme

1: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: I2 / diethyl ether / 4 h / Ambient temperature 3: NaBH4 / methanol / 0.25 h / 0 °C View Scheme

1: I2 / diethyl ether / 4 h / Ambient temperature 2: NaBH4 / methanol / 0.25 h / 0 °C View Scheme

1: imidazole / dimethylformamide / 2.5 h / 50 °C 2: diisobutylaluminium hydride / CH2Cl2 / 0.08 h / -78 °C 3: pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 4: 83 percent / 48percent aq. HF / acetonitrile / 2 h / Ambient temperature 5: 85 percent / pyridine / 4 h / Ambient temperature 6: t-BuOK / tetrahydrofuran 7: 100 percent / LiOH / propan-2-ol; H2O View Scheme