Synthesis
Acetonitrile (0.5 M), benzophenone imine (100 mg, 1 equiv), chiral epoxide (1 equiv), BHT (48.6 mg, 40 mol %), and Y(OTf)3 (29.6 mg, 10 mol %) were added to the reaction flask. The flask was capped and placed in an oil bath set to 60°C. The reaction mixture was stirred for 2 hours. 5 μL of the reaction mixture was diluted in 1.0 mL of acetonitrile and analyzed by HPLC until the reaction was complete. The reaction mixture was then allowed to cool to room temperature. HCl (1 M, 0.550 mL) and EtOAc (0.5 mL) were added to the mixture. The two-phase mixture was vigorously stirred at 60°C for 30 minutes to ensure that the mixture was acidic to litmus (pH < 4). The mixture was allowed to cool to room temperature. The layers were separated using a separatory funnel. The aqueous layer was transferred to a vial equipped with a magnetic stir bar to obtain (S)-1-amino-3-chloro-2-propanol hydrochloride.
Figure: Synthetic route of (S)-1-amino-3-chloro-2-propanol hydrochloride
