lithium aluminium tetrahydride in tetrahydrofuran T=-10°C;

1: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 2: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 3: H2, Et3N / 10percent Pd/C / methanol / 0.33 h / Ambient temperature 4: 34 percent / H2O, N-bromosuccinimide (NBS) / CHCl3 / 3 h / Ambient temperature View Scheme

1: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 2: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 3: 64 percent / H2 / 10percentPd/C / methanol / 24 h / Ambient temperature View Scheme

1: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 2: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 3: H2, Et3N / 10percent Pd/C / methanol / 0.33 h / Ambient temperature View Scheme