Aluminium lithium hydride → Benzyl 3-formylpiperidine-1-carboxylate

HRID 2115662Notes

Reaction equation

HRID 2115662 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:13]1)=[O:11]>C1COCC1>[CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22258974Benzyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate

Product 1

HCID 9899653Benzyl 3-formylpiperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) suspension of lithium aluminum hydride (0.70 g, 18.4 mmol) in dry THF (100 mL) under an argon atmosphere was added dropwise a solution of benzyl 3-{[methoxy(methyl)amino]carbonyl}-1-piperidinecarboxylate (4.5 g, 14.7 mmol) in THF (30 mL), and the stirring was continued at −78° C. for 45 min. The reaction mixture was quenched with 0.5N KHSO4 (130 mL), and then extracted with ether. The separated organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to give benzyl 3-formyl-1-piperidinecarboxylate as a colorless oil (0.54 g, yield; 82%).

Workup

  1. temperatureTo a cooled
  2. customThe reaction mixture was quenched with 0.5N KHSO4 (130 mL)
  3. extractionextracted with ether
  4. dry with materialThe separated organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7ace6d047794a90b6cd1cd31b0cae01
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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