Anisole → 6-Oxopiperidine-3-carboxylic acid

HRID 83512Notes

Reaction equation

HRID 83512 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH:8]([C:13]([OH:15])=[O:14])[CH2:7]1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[O:12]=[C:11]1[NH:6][CH2:7][CH:8]([C:13]([OH:15])=[O:14])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 63362718HCID 63362718, compound

Product 1

HCID 5600906-Oxopiperidine-3-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To an optically active compound of 1-(2,4-dimethoxybenzyl)-6-oxopiperidine-3-carboxylic acid (1.36 g) were added anisole (758 μl) and trifluoroacetic acid (10 ml), and the mixture was stirred at 80° C. for 6 hours. This reaction solution was cooled to room temperature, and then concentrated under reduced pressure. To the resulting residue was added diisopropyl ether, and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, and dried under reduced pressure to give the titled compound (628 mg).

Workup

  1. temperatureThis reaction solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resulting residue was added diisopropyl ether
  4. stirringthe mixture was stirred at room temperature
  5. filtrationThe insoluble substance was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-6d0a263c5ed645e0963f032a2bda4ef8
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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