Aluminium lithium hydride → HCID 58743350, Verbindung

HRID 722800

Reaktionsgleichung

Reaktionsgleichung von HRID 722800
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]([C@@H:22]([CH2:33][CH2:34][CH3:35])[C:23](OCC1C=CC=CC=1)=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:15]([N:14]([C@@H:22]([CH2:33][CH2:34][CH3:35])[CH2:23][OH:24])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 44223288(S)-benzyl 2-(dibenzylamino)pentanoate

Produkt 1

HCID 58743350HCID 58743350, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (0° C.) suspension of LiAlH4 (184 mg, 4.84 mmol) in THF (10 mL), a solution of ester 9 (375 mg, 0.97 mmol) in THF (2.5 mL) was added. The mixture was stirred at 0° C. for 2 h, and then quenched by dropwise addition of EtOH (3 ml). Na—K tartrate solution (10% aq, 30 mL) was added, and the crude was extracted with EtOAc (3×30 mL), dried over Na2SO4, concentrated in vacuo and purified by column chromatography on silica (hexane/EtOAc 5:1) to obtain alcohol 10 as a colorless oil (170 mg, 62% yield).

Aufarbeitung

  1. customquenched by dropwise addition of EtOH (3 ml)
  2. additionNa—K tartrate solution (10% aq, 30 mL) was added
  3. extractionthe crude was extracted with EtOAc (3×30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on silica (hexane/EtOAc 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-b237fdfe99ca4bf49e605cd7b24785e6
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138547B2

Verknüpfte Notizen

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