L-Tryptophan → Tryptophanol

HRID 2259296

Reaktionsgleichung

Reaktionsgleichung von HRID 2259296
[NH2:1][C@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][CH:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[CH2:13][OH:14]

Komponenten

4

Edukt 2

HCID 6305L-TryptophanHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10684Tryptophanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

L Tryptophan (10.2 g) was cautiously added in portions to a stirred solution of lithium aluminium hydride in tetrahydrofuran (1M, 150 ml). The reaction was stirred for 72 hours and then heated to reflux for 1 hour. The reaction mixture was cooled and then quenched carefully with 2N sodium hydroxide (150 ml). Ethyl acetate (500 ml) was added and the mixture was filtered through a pad of Celite. The organic phase was washed with water, dried (MgSO4) and evaporated to yield the crude title compound.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. customquenched carefully with 2N sodium hydroxide (150 ml)
  5. additionEthyl acetate (500 ml) was added
  6. filtrationthe mixture was filtered through a pad of Celite
  7. washThe organic phase was washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b0ad0d2884434937b8319f2bbf59ed84
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05472978

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