Sodium Nitrite → (S)-1-Phenyl-3-propanolamine

HRID 1416880

Reaktionsgleichung

Reaktionsgleichung von HRID 1416880
[C:1]1([C@H:7]([CH2:11][CH2:12][OH:13])C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]([O-])=O.[Na+]>OS(O)(=O)=O>[C:1]1([C@@H:7]([NH2:14])[CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 23668193Sodium NitriteHCID 53916301(S)-2-phenyl-4-hydroxybutanoic acid

Produkt 1

HCID 2734520(S)-1-Phenyl-3-propanolamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

The hydrazide of (S)-2-phenyl-4-hydroxybutanoic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (S)-1-phenyl-3-hydroxypropylamine is isolated as a light yellow oil.

Aufarbeitung

  1. extractionextraction of the reaction mixture with ethyl acetate
  2. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  3. dry with materialdrying of the extracts over MgSO4, filtration
  4. customthe removal of solvent
  5. customby rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-79eaa4db3303425a81c0d5260cfe2837
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916786

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