1.1: 97 percent / hydrogen / Pd/C / methanol / 6 h / 760 Torr 2.1: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; sodium hypochlorite; sodium chlorite / acetonitrile; aq. phosphate buffer / 6 h / 25 °C / pH 6.8 3.1: ethyl chloroformate; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 3.2: 75 percent / ammonium hydroxide / tetrahydrofuran / 16 h View Scheme

potassium hydroxide; potassium iodide in tert-butyl methyl ether T=20°C; 4 h; Product distribution / selectivity;

ammonia in dichloromethane T=-10°C; 3 h; Product distribution / selectivity;

2-hydroxy-pyridine in toluene T=80°C; 24 h; Product distribution / selectivity;

1: pyrrolidin-2-one With sodium methylate in methanol; toluene T=40°C; 2: (R)-2-bromobutyramide in tetrahydrofuran T=0 - 20°C; 17 h; Product distribution / selectivity;

1.1: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; sodium hypochlorite; sodium chlorite / acetonitrile; aq. phosphate buffer / 6 h / 25 °C / pH 6.8 2.1: ethyl chloroformate; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 75 percent / ammonium hydroxide / tetrahydrofuran / 16 h View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / |Inert atmosphere; |Reflux 2.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 20 °C / 3102.97 Torr 3.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 7 h / 35 °C / pH 6.7 3.2: 0.75 h / 20 °C / pH 8 3.3: pH 3 - 4 4.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 5.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C / |Inert atmosphere View Scheme

1.1: N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 0.33 h / 0 °C 1.2: 24 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / -78 °C 2.1: 140 mg / LiOH*H2O; H2O2 / tetrahydrofuran / 7 h / 0 °C 3.1: (C2H5)3N; ethyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C 3.2: 65 percent / ammonium hydroxide / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme

1.1: 140 mg / LiOH*H2O; H2O2 / tetrahydrofuran / 7 h / 0 °C 2.1: (C2H5)3N; ethyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 65 percent / ammonium hydroxide / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme

1.1: 141 mg / LiOH*H2O; H2O2 / tetrahydrofuran / 7 h / 0 °C 2.1: (C2H5)3N; ethyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C 2.2: ammonium hydroxide / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme