Aluminium lithium hydride → HCID 22329391, compound

HRID 586144Notes

Reaction equation

HRID 586144 reaction equation
CON(C)[C:4](=[O:13])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:7]1([CH2:6][CH2:5][CH:4]=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22329353HCID 22329353, compound

Product 1

HCID 22329391HCID 22329391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The above amide (1 equiv) is dissolved in dry THF and the solution is cooled to −78° C. Solid LAH (0.5 equiv) is carefully added. The reaction mixture is then immersed in an ice-bath at 0° C. and stirred 30 min. The reaction is quenched by the addition of EtOAc followed by water. The mixture is diluted with Et2O and the layers are separated. The organic is washed with brine, dried over Na2SO4, decanted and concentrated to yield 3-(piperid-1-yl)-propanal which is used immediately in the next step.

Workup

  1. customThe reaction mixture is then immersed in an ice-bath at 0° C.
  2. customThe reaction is quenched by the addition of EtOAc
  3. additionThe mixture is diluted with Et2O
  4. customthe layers are separated
  5. washThe organic is washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9cd17fda7bd40459e03f3c95112f6f1
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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