Diethyl Ether → 1-Boc-piperidine-3-carboxaldehyde

HRID 899054Notes

Reaction equation

HRID 899054 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[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][CH2:11][CH:10]([CH:14]=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Periodinane (18.2 g, 42.9 mmol) was added to 3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (7.10 g, 33.0 mmol) in CH2Cl2 (230 mL) and stirred for 90 min. Diethyl ether (230 mL) was added and precipitates were removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 230 mL). The organic layer was washed with 0.5 M NaOH solution and brine. The organic phase was dried and concentrated under reduced pressure to yield 3-Formyl-piperidine-1-carboxylic acid tert-butyl ester (6.50 g, 93%).

Workup

  1. customprecipitates
  2. customwere removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 230 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

Sources & evidence

ORD record
ord-9a4e8929b9754f05bf7b3fb6001657d8
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Reaction notes

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