Triphenylphosphine → (2S)-3-Phenylpropane-1,2-diamine

HRID 650678

Reaktionsgleichung

Reaktionsgleichung von HRID 650678
[N:1]([CH2:4][C@@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C@@H:5]([NH2:13])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 11769078(S)-1-azido-3-phenylpropan-2-amine

Produkt 1

HCID 12699301(2S)-3-Phenylpropane-1,2-diamineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A sample of the compound from step 4a (790 mg, 4.48 mmole) was dissolved in 30 mL of THF and 6 mL of water, triphenylphosphine (5.0 g, 19.1 mmole) was added, and the reaction mixture was stfired for 24 hours at reflux. The solvent was removed, and the residue was dissolved in 2 N HCl. NaCl was added, and the solution was extracted with ethyl ether. The aqueous layer was adjusted to pH 12 with K2CO3, saturated with NaCl, then extracted with GICl3 and CHCl3 containing 15% isopropanol. The solvent was removed under vacuum to afford 439 mg of the title compound. MS m/z (M+H)+: 151, MS m/z (M+NH4)+: 168.

Aufarbeitung

  1. temperatureat reflux
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 2 N HCl
  4. additionNaCl was added
  5. extractionthe solution was extracted with ethyl ether
  6. extractionextracted with GICl3 and CHCl3 containing 15% isopropanol
  7. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-afb21f95af18418e86f0c6e3317b7bc5
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274715B1

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