1: With diisobutylaluminium hydride in tetrahydrofuran; dichloromethane T=-78°C; 1 h; 2: With water in tetrahydrofuran; methanol; dichloromethane

sodium tetrahydroborate in ethanol T=0 - 20°C;

sodium tetrahydroborate; boric acid trimethyl ester; dimethyl sulfate in tetrahydrofuran T=20°C; 4.5 h;

bromine

1: Br2; AcOH 2: 59 percent / NaBH4 / ethanol / 0 - 20 °C View Scheme

1: N,N-dicyclohexylmethylamine; Pd0(tris(tert-butyl)phosphine)2 / 2-methyl tetrahydrofuran / 70 - 86 °C 2: 5 palladium on charcoal; hydrogen; sodium carbonate / 2-methyl tetrahydrofuran; ethanol / 50 °C / 750.08 Torr / |Inert atmosphere 3: 5 palladium on charcoal; hydrogen; sodium carbonate / water; toluene / 50 - 55 °C / 750.08 Torr / |Inert atmosphere 4: Vitride® / toluene / 5 - 25 °C / |Inert atmosphere; |Cooling with ice 5: (S)-α-hydroxybenzeneacetic acid / 2-methyl tetrahydrofuran / 70 °C 6: triethylamine; pyridine / dichloromethane / 10 - 20 °C 7: hydrogenchloride / water; acetonitrile / 1 h / 50 °C / pH 2 - 2.5 View Scheme

2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; copper diacetate in water; acetonitrile T=20°C; 4 h; Green chemistry;