1: toluene / 1.5 h / Heating 2: NaBH4 / methanol / 2 h / 40 °C View Scheme

1: toluene / 1.5 h / Heating 2: NaBH4 / methanol / 2 h / 40 °C View Scheme

ethanol

1: 80.7 percent / Et3N / diethyl ether / 5 h / Ambient temperature 2: 68.4 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 3: 87.3 percent / H2 / Raney-Ni / ethyl acetate / 16 h / 760 Torr / Ambient temperature 4: 88.8 percent / H2SO4 / CH2Cl2 / 0.5 h / 5 - 7 °C 5: 80.5 percent / glacial acetic acid / 4 h / Ambient temperature 6: H2, glacial acetic acid / 10percent Pd/C / 6 h / 50 °C View Scheme