borane-THF in tetrahydrofuran 3 h; Ambient temperature;

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 2 h 2: 64 percent / NaBH4 / propan-2-ol / 6 h / 70 °C 3: 45 percent / H2, 15percent aq. HCl / 5percent Pd/C / ethanol / 10 h / 760 Torr / Ambient temperature View Scheme

1: 1.) citric acid, 2.) ZnBr2, Na2CO3 / 1.) H2O, 1 h, 2.) H2O, RT, 2 h 2: ethanol / 48 h / Heating View Scheme

1: 1.) citric acid, 2.) ZnBr2, Na2CO3 / 1.) H2O, 1 h, 2.) H2O, RT, 2 h 2: ethanol / 48 h / Heating View Scheme

in ethanol 48 h; Heating;

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 2 h 2: 64 percent / NaBH4 / propan-2-ol / 6 h / 70 °C View Scheme