1: 1.) 15percent n-BuLi, (i-Pr)2NH / 1.) THF, hexane, -75 deg C, 30 min, 2.) -75 deg C, 1 h; up to r.t., 2 h 2: 1.) 15percent n-BuLi, (i-Pr)2NH / 1.) THF, hexane, -75 deg C, 10 min, 2.) -75 deg C, 1 h; up to r.t., 2 h 3: conc. HCl / tetrahydrofuran; hexane / 0.5 h / Ambient temperature View Scheme

1: NH2OH*HCl 2: 1.) 15percent n-BuLi, (i-Pr)2NH / 1.) THF, hexane, -75 deg C, 30 min, 2.) -75 deg C, 1 h; up to r.t., 2 h 3: 1.) 15percent n-BuLi, (i-Pr)2NH / 1.) THF, hexane, -75 deg C, 10 min, 2.) -75 deg C, 1 h; up to r.t., 2 h 4: conc. HCl / tetrahydrofuran; hexane / 0.5 h / Ambient temperature View Scheme

1: 1.) 15percent n-BuLi, (i-Pr)2NH / 1.) THF, hexane, -75 deg C, 10 min, 2.) -75 deg C, 1 h; up to r.t., 2 h 2: conc. HCl / tetrahydrofuran; hexane / 0.5 h / Ambient temperature View Scheme

lithium diisopropyl amide 1.) THF, hexane, -70 deg C, 1 h, 2.) THF, hexane, -70 deg C, 1 h; Yield given. Multistep reaction;

1: 1.) H2, 2.) AcOH / 1.) PtO2 / 1.) MeOH, RT, 1 atm, 1.5 h, 2.) 60 - 70 deg C, 2 h 2: 45 percent / diethyl ether; methanol / 3 h / 0 °C 3: 1.) LDA, 2.) n-BuONO / 1.) THF, hexane, -70 deg C, 45 min, 2.) THF, hexane, -70 deg C, 1 h View Scheme

1: 1.) H2, 2.) AcOH / 1.) PtO2 / 1.) MeOH, RT, 1 atm, 1.5 h, 2.) 60 - 70 deg C, 2 h 2: 45 percent / diethyl ether; methanol / 3 h / 0 °C View Scheme