1: With sodium cyanoborohydride; acetic acid in N,N-dimethyl-formamide T=20°C; 2 h; 2: With water; sodium hydroxide in N,N-dimethyl-formamide

1: N,N-dimethyl-formamide / Inert atmosphere; Reflux 2: water; methanol / 1 h / 20 °C / Inert atmosphere 3: hydrogen; ferrous acetate / 5 rhodium-on-charcoal / toluene; tetrahydrofuran / 48 h / 20 °C / 38002.6 Torr / Inert atmosphere 4: hydrogenchloride; Et3N-BH3 / 1,4-dioxane; water / 20 °C / Inert atmosphere; Reflux View Scheme

1: hydrogen; ferrous acetate / 5 rhodium-on-charcoal / toluene; tetrahydrofuran / 48 h / 20 °C / 38002.6 Torr / Inert atmosphere 2: hydrogenchloride; Et3N-BH3 / 1,4-dioxane; water / 20 °C / Inert atmosphere; Reflux View Scheme

triethylamine in dichloromethane T=20°C; Inert atmosphere;