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 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: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / |Inert atmosphere; |Reflux 2: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 20 °C / 3102.97 Torr View Scheme