1H-imidazole in N,N-dimethyl-formamide

1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 2 h; 2: With hydrogenchloride; water in tetrahydrofuran

pyridine T=25°C; 17 h;

4-(N,N-dimethlyamino)pyridine in DMF (N,N-dimethyl-formamide) T=0 - 5°C; 5 h;

hydrazine hydrate in ethanol 8 h; Ambient temperature;

sodium tetrahydroborate; copper(I) bromide 1.) EtOH, 15 min, room temperature, 2.) EtOH, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

sodium periodate in tetrahydrofuran; water T=30 - 40°C; 144 h;

1: 67 percent / 0.1N HCl / ethanol / 24 h / 0 °C 2: 71 percent / pyridine / 0.5 h / 80 °C 3: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C View Scheme

1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 - 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 3: potassium hydride / tetrahydrofuran / 0 - 20 °C View Scheme

1: 96 percent / 4-methylmorpholine N-oxide. 4A molecular sieves, tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 25 °C 2: 93 percent Turnov. / aq. K2CO3 / methanol / 2.5 h / 0 °C 3: 85 percent / pyridine / toluene / 0.5 h / 0 °C 4: 95 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 25 °C 5: tetrahydrofuran; cyclohexane / 15 h / -78 °C 6: 94 percent Turnov. / NaBH4 / methanol / 3 h / 25 °C 7: 86 percent Turnov. / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 0 °C 8: 80 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 25 °C View Scheme