Methanol → (R)-beta-aminophenethyl alcohol

Participants

Reaction Steps

20 g (920 mmol) of lithium borohydride were dissolved in 420 ml of absolute THF. 233.5 ml (1.84 mol) of trimethylchlorosilane were added dropwise with stirring and 69.5 g (0.46 mol) of (R)-phenylglycine were then added in portions in the course of 4 hours. The reaction mixture was stirred overnight at room temperature. 690 ml of methanol were then added, and the mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in 690 ml of 20% strength aqueous potassium hydroxide solution with stirring. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated in vacuo. Yield: 41.2 g (65.3%).

Provenance & Evidence