Water → (S)-1-Phenyl-3-propanolamine

HRID 2270109

Reaktionsgleichung

Reaktionsgleichung von HRID 2270109
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[NH2:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11](OCC)=[O:12].O>C1COCC1>[NH2:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][CH2:11][OH:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22831526(S)-Ethyl 3-amino-3-phenylpropanoate hydrochloride

Produkt 1

HCID 2734520(S)-1-Phenyl-3-propanolamineAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.45 g (38.1 mmol) of lithium aluminum hydride were added in portions with ice-cooling to a suspension of 3.5 g (15.2 mmol) of ethyl (S)-3-amino-3-phenyl-propionate hydrochloride in 150 ml of absolute THF and the mixture was stirred at room temperature for 1 hour. 5 ml of water were then cautiously added dropwise the ice-cooling. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was taken up in DCM and the solution was extracted with water. The organic phase was dried over sodium sulfate. After filtration and removal of the solvent in vacuo, 1.84 g of (S)-3-amino-3-phenylpropanol were obtained.

Aufarbeitung

  1. temperaturecooling
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionthe solution was extracted with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationAfter filtration and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9377120d2e36490e94eaf93b0066a762
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331552B1

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