4-pyrrolidin-1-ylpyridine; triethylamine in dichloromethane Ambient temperature;

C20H25N2(1+)*Cl(1-); water; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile T=20°C; 16 h; Schlenk technique; chemoselective reaction;

phosphorus tribromide in chloroform T=20°C; 3 h;

D-glucose; E. coli JM109 in 2,2,4-trimethylpentane; isopropyl alcohol T=30°C;

manganese(IV) oxide in tetrahydrofuran T=45°C; Rate constant;

1: 8.98 g / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / Ambient temperature 2: 30 percent / p-toluenesulfonic acid / benzene / 3.5 h / Heating 3: 1 M MeONa / 1.) methanol, -78 deg C, 10 min, 2.) -78 deg C, 2 h 4: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 5: 76 percent / MnO2 / ethyl acetate / Ambient temperature 6: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 0.5 h, 2.) room temperature, 2 h 7: 50 percent / LiOH, water / 1,2-dimethoxy-ethane / 3 h / Ambient temperature View Scheme

1: 8.98 g / triethylamine, 4-pyrrolidinopyridine / CH2Cl2 / Ambient temperature 2: 36 percent / p-toluenesulfonic acid / benzene / 3.5 h / Heating 3: 1 M MeONa / 1.) methanol, -78 deg C, 10 min, 2.) -78 deg C, 2 h 4: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 5: 74 percent / MnO2 / ethyl acetate / Ambient temperature 6: 91 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 0.5 h, 2.) room temperature, 2 h View Scheme

N-butylamine in benzene 1 h; Reflux; Time;

sodium tetrahydroborate in ethanol T=0°C;

tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) in toluene T=50°C; P=760 Torr;