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

Multi-step reaction with 8 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature7: Et3N / CH2Cl2 / 1 h / 0 °C8: LiBr / tetrahydrofuran / Ambient temperature  

With  lithium bromide in  tetrahydrofuran  Ambient temperature;  Yield given;   

Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h / 0 °C2: LiBr / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 4 steps 1: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h2: 72 percent / TsOH, MeOH / 4 h / Ambient temperature3: Et3N / CH2Cl2 / 1 h / 0 °C4: LiBr / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 6 steps 1: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C2: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature3: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h4: 72 percent / TsOH, MeOH / 4 h / Ambient temperature5: Et3N / CH2Cl2 / 1 h / 0 °C6: LiBr / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 3 steps 1: 72 percent / TsOH, MeOH / 4 h / Ambient temperature2: Et3N / CH2Cl2 / 1 h / 0 °C3: LiBr / tetrahydrofuran / Ambient temperature