Aluminium lithium hydride → Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol

HRID 1378651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378651
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[N:6]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:16]([N:6]1[CH:5]([CH2:4][CH2:3][OH:2])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydride2×HCID 54110926Racemic (2-Benzyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-3-yl)-acetic acid methyl ester

Produkt 1

HCID 22911385Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a well-stirred ice-bath-chilled solution of the racemic mixture of Step C (650 mg, 2.0 mmol) in anhydrous tetrahydrofuran (10 ml), a solution of lithium aluminum hydride in tetrahydrofuran (6.11 ml of a 1.0M solution, 6.11 mmol of lithium aluminum hydride) was added dropwise over 5 minutes. The reaction mixture was then stirred for 24 hours at ambient temperature before being ice-bath-chilled and cautiously quenched with 15% aqueous sodium hydroxide (2 ml). Anhydrous sodium sulfate was added to dry the mixture, which was then filtered. The filtrate was concentrated in vacuo to afford the title compound as a colorless oil in quantitative yield.

Aufarbeitung

  1. temperaturebath-chilled
  2. customcautiously quenched with 15% aqueous sodium hydroxide (2 ml)
  3. additionAnhydrous sodium sulfate was added
  4. customto dry the mixture, which
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2548e090e584d46b953b9ad36b12e72
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668145

Notizen zur Reaktion

Wird geladen…