Ethyl acetate hexane → (S)-2-(dibenzylamino)pentanal

HRID 1099511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099511
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:15]([CH2:22][CH2:23][CH3:24])[C:16](N(OC)C)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH2:25]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:15]([CH2:22][CH2:23][CH3:24])[CH:16]=[O:17])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 44223340(S)-2-(dibenzylamino)-N-methoxy-N-methylpentanamide

Produkt 1

HCID 44223341(S)-2-(dibenzylamino)pentanalAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To anhydrous tetrahydrofuran (1.5 L) previously cooled to −20° C. to −30° C. was added solid lithium aluminum hydride (33.5 g; 0.882 mol; 120 mole %) slowly with stirring. A solution of (S)-2-(dibenzylamino)-N-methoxy-N-methylpentanamide (6) (250 g; 0.735 mol) in anhydrous tetrahydrofuran (1 L) at −30° C. was slowly added to the above mixture under a nitrogen atmosphere. The reaction was continued for 2 hours at −30° C., monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:9). Upon completion of the reaction, the excess reagent was quenched by the dropwise addition of ethyl acetate (1 L) and ice-cold water (300 ml) at −30° C. The insoluble salts were filtered through celite, the filtrate diluted with water (3 L), and the product extracted into ethyl acetate (2 L). The combined ethyl acetate layers were washed with water (2 L), dried over sodium sulfate, filtered, and solvent removed under reduced pressure to provide (S)-2-(dibenzylamino)pentanal (7) (195 g) as a light yellow oil, which was used without purification in the next step.

Aufarbeitung

  1. customUpon completion of the reaction
  2. customthe excess reagent was quenched by the dropwise addition of ethyl acetate (1 L) and ice-cold water (300 ml) at −30° C
  3. filtrationThe insoluble salts were filtered through celite
  4. additionthe filtrate diluted with water (3 L)
  5. extractionthe product extracted into ethyl acetate (2 L)
  6. washThe combined ethyl acetate layers were washed with water (2 L)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customsolvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-89d798f1f0da431db63a6db371f79aba
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143448B2

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