Benzaldehyde → HCID 29949005, compound

Participants

Reaction Steps

Triethylamine (9.5 ml, 68.0 mmol) and benzaldehyde (6.37 ml, 63.0 mmol) were added to a methanol (300 ml) solution of methyl O-tert-butyl-L-serinate hydrochloride (12.0 g, 57.0 mmol) and the resulting mixture was stirred at room temperature for 6 hours. Sodium borohydride (3.23 g, 86.0 mmol) was gradually added under ice cooling and then the resulting mixture was stirred at room temperature for 2 hours. An aqueous solution of saturated ammonium chloride (100 ml) was added to the reaction mixture. After concentration under reduced pressure, the residue was diluted with ethyl acetate and the precipitated insoluble matter was removed by filtration. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.3 g, 100%) as a colorless oil.

Provenance & Evidence