1: pyridine / CH2Cl2 / 15 h / 4 °C 2: NaI, NaHCO3 / acetone / 3 h / Heating 3: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 4: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 5: pyridine / CH2Cl2 / 14 h / 4 °C 6: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 7: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 8: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

lithium aluminium tetrahydride in diethyl ether 2 h; Ambient temperature;

1: 83 percent / imidazole / dimethylformamide 2: 87 percent / lithium aluminum hydride / diethyl ether View Scheme

1: sodium hydroxide / H2O; dioxane / 0.5 h / 20 °C 2: 6.84 g / imidazole; DMAP / dimethylformamide / 1 h / 50 °C 3: 52 percent / LiAlH4 / diethyl ether / 1.92 h / 0 - 20 °C View Scheme

1: 95 percent / sodium borohydride / tetrahydrofuran; H2O 2: 83 percent / imidazole / dimethylformamide 3: 87 percent / lithium aluminum hydride / diethyl ether View Scheme

1: pyridine / 21 h / Ambient temperature 2: 90 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 3: 72 percent / Na, NH3 (liquid) / tetrahydrofuran / 1.5 h / -35 °C View Scheme

1: 90 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 2: 72 percent / Na, NH3 (liquid) / tetrahydrofuran / 1.5 h / -35 °C View Scheme

1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=20°C; 3 h;

1: 97 percent / 4-(N,N-dimethylamino)pyridine; triethylamine / CH2Cl2 2: 89 percent / lithium bromide; sodium bicarbonate / acetone View Scheme