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

HRID 1611137Notes

Reaction equation

HRID 1611137 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%). [Starting Compound 2D]

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-e2761fcfc7654569b2eeb406c1723ab0
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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