Tridecanal → Methyl 3-tridecylaminopropionate

HRID 1872802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872802
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl.[NH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH2:1]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 25311TridecanalHCID 517045Sodium AcetateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 18687169Methyl 3-tridecylaminopropionateAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of tridecanal (1.0 g), methyl 3-aminopropionate hydrochloride (704 mg), and sodium acetate (414 mg) in methanol (20 ml) was added sodium cyanoborohydride (317 mg). After stirring for 45 minutes, the mixture was quenched with water (20 ml), concentrated, and extracted with ethyl acetate (40 ml). The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was purified on silica gel, eluting with 5% methanol in chloroform to give methyl 3-tridecylaminopropionate (0.78 g).

Aufarbeitung

  1. customthe mixture was quenched with water (20 ml)
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (40 ml)
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel
  8. washeluting with 5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e5abfdbc0abf41a093719ba20cb5e680
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06110933

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