Diethyl Ether → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 899057Notes

Reaction equation

HRID 899057 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Periodinane (26.9 g, 63.5 mmol) was added to 4-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (10.5 g, 48.8 mmol) in CH2Cl2 (200 ml) and stirred for 90 min. Diethyl ether (560 mL) was added and precipitates were removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL). The organic layer was washed with 0.5 M NaOH solution and brine. The organic phase was dried and concentrated under reduced pressure. Purification using flash chromatography (hexane/EtOAc, 8:2) gave 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester (8.5 g, 81%).

Workup

  1. customprecipitates
  2. customwere removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL)
  3. washThe organic layer was washed with 0.5 M NaOH solution and brine
  4. customThe organic phase was dried
  5. concentrationconcentrated under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-85995b61ffd44edc9d8cddaf357894cd
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Reaction notes

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