Sodium Hydroxide → 1-(Cyclopropylcarbonyl)piperidine-4-carboxylic acid

HRID 1260965Notes

Reaction equation

HRID 1260965 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][CH:9]([C:12]([O:14]CC)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]([N:6]2[CH2:7][CH2:8][CH:9]([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10036613Ethyl 1-(cyclopropylcarbonyl)piperidine-4-carboxylate

Product 1

HCID 89029151-(Cyclopropylcarbonyl)piperidine-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (6.3 g) obtained in step 4 in ethanol (30 mL) was added 4N aqueous sodium hydroxide solution (35 mL), and the mixture was stirred at room temperature for 22 hr. The reaction mixture was concentrated under reduced pressure, and made acidic with 6N hydrochloric acid. The resultant product was extracted with ethyl acetate, the organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure to give 1-(cyclopropylcarbonyl)piperidine-4-carboxylic acid (5.21 g, 95%) as a pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe resultant product was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6cd70335563140fd9ea2cbe21af12742
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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