Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate → Ethyl 4-formylpiperidine-1-carboxylate

HRID 586138Notes

Reaction equation

HRID 586138 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 19773576Ethyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 14989210Ethyl 4-formylpiperidine-1-carboxylateYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol (7.5 g, 40.0 mmol, 1.0 equiv) was dissolved in 500 mL of CH2Cl2. Pyridinium chlorochromate (12.96 g, 60.1 mmol, 1.5 equiv) was added and resulting mixture was stirred for 16 h. The dark liquid was decanted and the solvent was removed in vacuo. The residue was triturated with 500 mL of diethyl ether and the mixture was filtered. The filtrate was washed with 150 mL of 1 N HCl and dried over Na2SO4. The liquid was decanted and concentrated by rotary evaporation to yield 4-formyl-piperidine-1-carboxylic acid ethyl ester as a light brown oil (6.1 g).

Workup

  1. customresulting mixture
  2. customThe dark liquid was decanted
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with 500 mL of diethyl ether
  5. filtrationthe mixture was filtered
  6. washThe filtrate was washed with 150 mL of 1 N HCl
  7. dry with materialdried over Na2SO4
  8. customThe liquid was decanted
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1d456c17a6234e8ca515b557255400ae
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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