Ethyl 1-phenylpiperidine-4-carboxylate → 1-Phenylpiperidine-4-carbaldehyde

HRID 1068428Notes

Reaction equation

HRID 1068428 reaction equation
[C:1]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(OCC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[CH:1]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)=[O:2]

Participants

5

Reactant 2

HCID 6470Ethyl 1-phenylpiperidine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 138429921-Phenylpiperidine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product from Example 28, Step C is dissolved in THF and cooled to −78° C. under nitrogen. A solution of diisobutylaluminum hydride (1 eq.) in toluene is added dropwise. After 30 min, the reaction is quenched with saturated sodium potassium tartrate solution. The mixture is extracted with ethyl acetate, and the organic phase washed with saturated brine, and dried over MgSO4. Filtration and concentration provides the title compound

Workup

  1. customthe reaction is quenched with saturated sodium potassium tartrate solution
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic phase washed with saturated brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4c33572b981449f3a3679a6c3c1f1327
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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