1: NaBH4, CeCl3 / methanol / 0.17 h / 20 °C 2: 80percent aq. formic acid / 0.67 h / 80 - 85 °C View Scheme

triethylamine; palladium on activated charcoal in toluene T=140°C; 16 h;

1.1: trimethyl orthoformate; p-toluenesulfonic acid hydrate; mol. sieves / CH2Cl2 / 15 h / 20 °C 2.1: Li; N,N-dimethyl-1-naphthylamine / tetrahydrofuran / 2 h / -65 °C 2.2: tetrahydrofuran / -65 - 20 °C 2.3: 12 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme