hydrogen; palladium in methanol; acetic acid

sodium dithionite; sodium carbonate in water; acetonitrile T=50°C; 1 h;

1: 60.9 percent / triethylamine / CCl4; ethyl acetate / 24 h / 23 °C 2: 93.4 percent / H2 / 10percent Pd/C / methanol; acetic acid / 3 h / 23 °C / 2068.6 Torr View Scheme

1: N-methylmorpholine / tetrahydrofuran / 0.03 h / 20 °C 2: 1H-tetrazole / tetrahydrofuran / 0.33 h / 20 °C 3: I2, H2O / tetrahydrofuran / 0.17 h / -40 °C 4: 30percent aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 1) 1H-tetrazole, 2) 85percent m-chloroperoxybenzoic acid / 1) THF, 20 deg C, 20 min, 2) 20 deg C, 10 min 2: 75 percent / sodium dithionite, sodium carbonate / acetonitrile; H2O / 1 h / 50 °C View Scheme