Benzaldehyde → methyl (2R)-2-(benzylamino)propanoate

To a solution of D-alanine methyl ester hydrochloride (3.0 g, 21.5 mmol) in methanol (10 mL) is added benzaldehyde (2.3 mL, 22.6 mmol). The reaction mixture is stirred at room temperature for 3 hours. The solvent is then evaporated. To the resultant residue is added acetic acid (15 mL) and methanol (1 mL) followed by portionwise addition of sodium cyanoborohydride (1.35 g, 21.5 mmol) at room temperature. The mixture is stirred overnight, and then the solvent is evaporated. The remaining residue is diluted with water (75 mL) and basified with Na2CO3. The mixture is extracted with ethyl acetate (3x75 mL). The combined organic extracts are washed with brine (50 mL), dried (Na2SO4), and the solvent is evaporated to give N-benzyl-D-alanine methyl ester.

1. customThe solvent is then evaporated
2. additionTo the resultant residue is added acetic acid (15 mL) and methanol (1 mL)
3. stirringThe mixture is stirred overnight
4. customthe solvent is evaporated
5. additionThe remaining residue is diluted with water (75 mL)
6. extractionThe mixture is extracted with ethyl acetate (3x75 mL)
7. washThe combined organic extracts are washed with brine (50 mL)
8. dry with materialdried (Na2SO4)
9. customthe solvent is evaporated

ORD record

ord-ac2d1852450d450bb22a3db77e765795

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552419