triethylamine; 4-(N,N-dimethlyamino)pyridine in dichloromethane T=20°C;

1: 1.) NaH / 1.) HMPA, 21 deg C, 2.) HMPA, 3 h 2: 60 percent / NaBH4 / aq. ethanol / 4 h / 21 °C View Scheme

1: 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde With sodium hydride in tetrahydrofuran T=0 - 20°C; 2: methyl iodide in tetrahydrofuran 2 h;

1,4-diaza-bicyclo[2.2.2]octane in N,N-dimethyl-formamide T=90 - 92°C; 23 h;

1: With 1-hydroxy-pyrrolidine-2,5-dione; o-iodoxybenzoic acid in dimethyl sulfoxide T=20°C; 16 h; 2: With hydrogenchloride; water; sodium chloride in dimethyl sulfoxide pH=3 - 4;

1: 1.) NaH / 1.) HMPA, 21 deg C, 2.) HMPA, 3 h 2: 60 percent / NaBH4 / aq. ethanol / 4 h / 21 °C 3: 45 percent / Ph3P, CCl4 / dimethylformamide / 108 h / 21 °C 4: 96 percent / NaI / acetone / 24 h / 21 °C 5: 1.) potassium bis(trimethylsilyl)amide / 1.) toluene, THF, HMPA, -100 to -78 deg C, 30 min, 2.) THF, -100 deg C, 3 h 6: 69 percent / hydroxylamine hydrochloride, Na acetate / aq. ethanol / 72 h / 21 °C 7: 69 percent / trifluoroacetic acid / 2 h / 21 °C View Scheme

sodium hydride in tetrahydrofuran T=20°C; 2 h;

1: ammonium acetate / 5 h / Reflux; Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

sodium cyanoborohydride; acetic acid in methanol T=60°C; pH=5; 18 h;