1: 90 percent / hydrogen / 4percent Pd/C / methanol; acetic acid / 2585.7 Torr / Ambient temperature 2: determination of e.e. (86percent) View Scheme

Multi-step reaction with 3 steps 1: 1) t-butyllithium / 1) THF, pentane, -100 deg C, 0.5 h, 2) THF, pentane, -100 deg C, 0.5 h2: hidrazine / aq. ethanol; acetic acid / 50 °C3: 2.) NaBH4 / 1) MeOH, RT, 0.2 h, 2) MeOH, 1 h