1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 2: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 3: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: Et3N / CH2Cl2 / 1 h / 0 °C 2: LiBr / tetrahydrofuran / Ambient temperature 3: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 4: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 5: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 2: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 3: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 2: 72 percent / TsOH, MeOH / 4 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / 0 °C 4: LiBr / tetrahydrofuran / Ambient temperature 5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 6: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 7: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C 2: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature 3: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 4: 72 percent / TsOH, MeOH / 4 h / Ambient temperature 5: Et3N / CH2Cl2 / 1 h / 0 °C 6: LiBr / tetrahydrofuran / Ambient temperature 7: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 8: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 9: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: LiBr / tetrahydrofuran / Ambient temperature 2: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 3: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 4: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 2: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: 72 percent / TsOH, MeOH / 4 h / Ambient temperature 2: Et3N / CH2Cl2 / 1 h / 0 °C 3: LiBr / tetrahydrofuran / Ambient temperature 4: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 5: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 6: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature 2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature 3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature 5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature 7: Et3N / CH2Cl2 / 1 h / 0 °C 8: LiBr / tetrahydrofuran / Ambient temperature 9: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 10: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 11: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme