1: 84 percent / formic acid / 24 h / 40 °C 2: 91 percent / toluene / 16 °C / Heating 3: 1) t-butyllithium / 1) THF, pentane, -100 deg C, 0.5 h, 2) THF, pentane, -100 deg C, 0.5 h 4: hidrazine / aq. ethanol; acetic acid / 50 °C 5: 2.) NaBH4 / 1) MeOH, RT, 0.2 h, 2) MeOH, 1 h 6: 90 percent / hydrogen / 4percent Pd/C / methanol; acetic acid / 2585.7 Torr / Ambient temperature 7: determination of e.e. (86percent) View Scheme

1: 6.96 g / aq. K2CO3 / 1.5 h / 20 °C 2: 100 percent / p-toluenesulfonic acid / CH2Cl2 / Heating 3: 100 percent / H2; HCO2H / 10 percent Pd/C / methanol / 30 h / 20 °C / 760 Torr View Scheme

acetic acid; trifluoroacetic acid

5percent aq. NaOH in dichloromethane T=20°C; Schotten-Baumann reaction; 2 h;