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

HRID 355443

Reaktionsgleichung

Reaktionsgleichung von HRID 355443
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 10987118methyl (2R)-2-(benzylamino)propanoateAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d51e808d470d484fba0e0f7eeb603f79
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05830915

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