1: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 2: pyridine / 1 h / Ambient temperature 3: 94 mg / POCl3 / toluene / 1 h / Heating View Scheme

1: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 2: pyridine / 1 h / Ambient temperature 3: 94 mg / POCl3 / toluene / 1 h / Heating 4: 82 percent / 10percent palladium on carbon / decahydronaphthalene / 1.5 h / Heating View Scheme

1: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 2: pyridine / 1 h / Ambient temperature View Scheme

sodium tetrahydroborate in methanol T=0°C; 0.5 h;