1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 1.2: 18 h / 20 °C 2.1: C19H23BNO3(1-)*H(1+); borane-THF / 1,4-dioxane / 72 h / |Inert atmosphere View Scheme

borane-THF; C19H23BNO3(1-)*H(1+) in 1,4-dioxane 72 h; Inert atmosphere; enantioselective reaction;

1.1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / pH 5 / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 18 h / 20 °C 3.1: C19H23BNO3(1-)*H(1+); borane-THF / 1,4-dioxane / 72 h / |Inert atmosphere View Scheme