1: 96 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: H2; glacial AcOH / Pd/C / ethanol; H2O / 18 h / 25 °C / 2585.74 Torr View Scheme

sodium cyanoborohydride; acetic acid 3 h; Ambient temperature;

1: pyridine / CH2Cl2 / 2 h 2: NaH / dimethylformamide / 0 °C 3: TiCl4 / toluene / 2 h 4: aq. NaOH / ethanol / 0.5 h / Heating 5: glac. AcOH, sodium cyanoborohydride / 3 h / Ambient temperature View Scheme

1: NaH / dimethylformamide / 0 °C 2: TiCl4 / toluene / 2 h 3: aq. NaOH / ethanol / 0.5 h / Heating 4: glac. AcOH, sodium cyanoborohydride / 3 h / Ambient temperature View Scheme