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

HRID 1378651Notes

Reaction equation

HRID 1378651 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f2548e090e584d46b953b9ad36b12e72
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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