4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane

1: (nBu)3N / heptane; toluene / 80 - 90 °C 2: LiOH*H2O / methanol / 2 h 3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 5: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 6: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 7: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 3: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 4: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 5: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

1: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 2: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 3: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 4: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 3: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

1: LiOH*H2O / methanol / 2 h 2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C 4: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 5: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 6: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

1: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 2: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme

pyridine in dichloromethane T=22°C; 1 h;

aluminum oxide in dichloromethane 0.05 h; microwave irradiation;