1: iodine; sodium hydrogencarbonate / ethanol; water / 20 °C 2: acetic acid; acetic anhydride; trifluorormethanesulfonic acid / 20 °C 3: sodium tetrahydroborate / dichloromethane; methanol / 20 °C View Scheme

With  palladium on activated charcoal; hydrogen; triethylamine in  tetrahydrofuran T=20°C; P=750.075 Torr;   

Multi-step reaction with 2 steps 1: tetrafluoroboric acid diethyl ether complex / 1,2-dichloro-ethane / 90 °C2: hydrogen; palladium on activated charcoal; triethylamine / tetrahydrofuran / 20 °C / 750.08 Torr  

With  iodine; sodium hydrogencarbonate in  ethanol; water T=20°C;