N-Benzyl-5-hydroxycyclohex-3-enecarboxamide → 5-[(Benzylamino)methyl]cyclohex-2-en-1-ol

HRID 597964Notes

Reaction equation

HRID 597964 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15]([CH:17]1[CH2:22][CH:21]([OH:23])[CH:20]=[CH:19][CH2:18]1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([NH:14][CH2:15][CH:17]1[CH2:22][CH:21]([OH:23])[CH:20]=[CH:19][CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 15064680N-Benzyl-5-hydroxycyclohex-3-enecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 150646815-[(Benzylamino)methyl]cyclohex-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.50 g, 40.5 mmol) in dry THF (100 ml), cooled in an ice bath, was added drop-wise a solution of N-benzyl-5-hydroxycyclohex-3-enecarboxamide (4.6 g, 20 mmol) in THF (60 ml) over 30 min. The cold bath was removed and the reaction was heated under reflux for 16 h. Then the mixture was cooled in an ice bath and diluted with ether (200 ml), then carefully quenched with water (1.5 ml), 1N sodium hydroxide (4 ml) and water (1.5 ml), successively. After stirring for 45 min, the white suspension was filtered through a glass frit, and the residue was washed with ether. Removal of solvents by rotary evaporation gave the alcohol as a clear, colorless oil (3.8 g, 88%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe cold bath was removed
  3. temperaturethe reaction was heated
  4. temperatureunder reflux for 16 h
  5. temperatureThen the mixture was cooled in an ice bath
  6. additiondiluted with ether (200 ml)
  7. customcarefully quenched with water (1.5 ml), 1N sodium hydroxide (4 ml) and water (1.5 ml)
  8. filtrationthe white suspension was filtered through a glass frit
  9. washthe residue was washed with ether
  10. customRemoval of solvents
  11. customby rotary evaporation

Sources & evidence

ORD record
ord-6e5af881b5094d6484ae34643c537839
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

Loading…