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

HRID 355443Notes

Reaction equation

HRID 355443 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH2:5].C([O-])(=O)C.[Na+].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH:5][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 89020methyl D-alaninateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10987118methyl (2R)-2-(benzylamino)propanoateYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

D-Alanine methyl ester (4 g, 28.66 mmol) is taken up in methanol (100 mL). To this is added sodium acetate (5.88 g, 71.65 mmol) and benzaldehyde (2.9 mL, 28.66 mmol). The mixture is stirred for 15 minutes and then a solution of sodium cyanoborohydride (1.08 g, 17.2 mmol) in methanol (5 mL) is added dropwise to the mixture. After stirring for 2 hours methanol is evaporated under reduced pressure and the product is extracted into ether and washed with water (2×). The crude product is purified by silica gel flash chromatography (8:2 hexane:ethyl acetate) to give 3.3 g of N-benzyl D-alanine methyl ester as an oil.

Workup

  1. customis evaporated under reduced pressure
  2. extractionthe product is extracted into ether
  3. washwashed with water (2×)
  4. customThe crude product is purified by silica gel flash chromatography (8:2 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-d51e808d470d484fba0e0f7eeb603f79
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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