Benzaldehyde → HCID 67269069, compound

Participants

Reaction Steps

To (2R,3S)-2-amino-3-hydroxybutanoic acid (14.7 g, 123 mol) in NaOH (50%, 70 mL) was added benzaldehyde (14 mL, 123 mmol). The white slurry was stirred at room temperature for 18 h and then cooled to 0° C. NaBH4 (675 mg, 17.9 mmol) was added in two portions over 10 minutes Cooling bath was removed and the thick slurry was stirred at room temperature for 40 minutes and addition NaBH4 (659 mg, 17.4 mmol) was added and stirred at 0° C. for 40 minutes Benzaldehyde (10 mL, 99 mmol) was added, cooled to 0° C. and additional NaBH4 (700 mg, 18.5 mmol) was added. After 5 minutes warmed up to room temperature and stirred for 2 hour. The reaction mixture was acidified with HCl (conc.) to pH of (about 3) and then filtered precipitate, washed with cold water and dried to give (2R,3S)-2-(benzylamino)-3-hydroxybutanoic acid (3.4 g, 13.2%) of white solid. MS [M+H] found 210.

Provenance & Evidence