alpha-Cyanocinnamic acid ethyl ester → Ethyl 3-amino-2-benzylpropanoate

HRID 1510230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510230
[C:1](/[C:3](=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:2][CH2:1][CH:3]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

4

Edukt 1

HCID 668187alpha-Cyanocinnamic acid ethyl ester

Produkt 1

HCID 19611763Ethyl 3-amino-2-benzylpropanoateAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl (2E)-2-cyano-3-phenylacrylate (1.2 g) in ethanol (30 mL) was added 10% Palladium hydroxide (0.3 g) and the mixture was hydrogenated at 3 atms. for 2 hours. After removing the catalysts by filtration on celite pad, the filtrate was evaporated in vacuo. The residue was dissolved in 1N HCl (2 mL) and washed with chloroform. The separated aqueous layer was adjusted to pH=7 by addition of saturated sodium bicarbonate solution and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford ethyl 3-amino-2-benzylpropanoate (388 mg).

Aufarbeitung

  1. customAfter removing the catalysts
  2. filtrationby filtration on celite pad
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in 1N HCl (2 mL)
  5. washwashed with chloroform
  6. additionThe separated aqueous layer was adjusted to pH=7 by addition of saturated sodium bicarbonate solution
  7. extractionextracted with ethyl acetate
  8. washThe separated organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-57b51a4d64294f60ae969601198ac125
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211919B2

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