sodium tetrahydroborate in ethanol 5 h;

sodium hydroxide T=90°C; 2 h;

1: hydrogenchloride; sodium nitrite / water 2: sodium tetrahydroborate View Scheme

1: hydrogenchloride; sodium nitrite / water 2: sodium tetrahydroborate View Scheme

1.1: thionyl chloride; benzotriazol-1-ol / dichloromethane 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere 2.2: 20 - 60 °C 3.1: water; sodium hydroxide / methanol / 20 h / 20 °C 4.1: toluene / 2 h / Reflux 5.1: hydrogenchloride / 1,4-dioxane / 4 h / Reflux 6.1: phenylalanine ammonia-lyase / 192 h / 30 °C / pH 8.8 / aq. buffer; Inert atmosphere; Enzymatic reaction View Scheme