sodium acetate; sodium cyanoborohydride in methanol 24 h; Ambient temperature;

1: 83 percent / pyridinium-hydrobromide-perbromide / pyridine / 2 h / 45 °C 2: 93 percent / NaBH4 / tetrahydrofuran / 1 h / 20 °C View Scheme

potassium carbonate in acetone 5 h; Heating;

bis-triphenylphosphine-palladium(II) chloride; potassium carbonate in N,N-dimethyl-formamide T=130°C; 12 h; Inert atmosphere;

manganese(II) nitrate hexahydrate in ethanol T=20°C; 0.2 h;

1: K2CO3 / ethanol / 10 h / Heating 2: NaOEt / ethanol; tetrahydrofuran / a) -15 deg C, 3 h, b) 4 deg C, 12 h 3: xylene / 3 h / Heating 4: 93 percent / KOH / ethanol / 1.5 h / Heating 5: 73 percent / copper chromite / quinoline / 3 h / 230 °C 6: acetic acid / CH2Cl2 / 2 h / Ambient temperature 7: 1.) iodomethane / 1.) THF, from 0 deg C to 4 deg C, 30 h, 2.) water, 80 deg C, 3.5 h 8: H2, NH3 / Raney nickel / ethanol / 48 h / 2508 Torr / Ambient temperature 9: 1.) NaOEt / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, RT, 3 h 10: H2 / 10percent Pd/C / ethanol / 48 h / 2508 Torr / Ambient temperature 11: Fremy's salt, aq. KH2PO4 / acetone / 4 h / 0 °C 12: 1.) t-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 3 h 13: p-toluenesulfonic acid / acetonitrile / 5 h / Ambient temperature 14: NaHCO3 / ethanol / 3 h / Heating 15: CH2Cl2 / 3 h / Ambient temperature 16: PhI(OCOCF3)2 (PIFA) / various solvent(s) / 0.33 h / Ambient temperature View Scheme

N-bromosuccinmide in N,N-dimethyl-formamide T=0°C; 0.25 h;

pyridinium hydrobromide perbromide in pyridine T=50°C; 2 h;

pyridine; pyridinium hydrobromide perbromide T=50°C; 2 h;

T=0°C;