Water → 1-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

HRID 352220Notes

Reaction equation

HRID 352220 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.O.[C:11](=[O:14])([O-])[O-:12].[K+].[K+]>C1COCC1>[C:3]([O:12][C:11]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)=[O:14])([CH3:7])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4498Nipecotic AcidHCID 11430Potassium Carbonate

Product 1

HCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of nipecotic acid, 2.0 g (16.0 mmol) in 20 mL of THF and 20 mL of water was added 4.7 g (33.6 mmol) of potassium carbonate and 3.5 g (16.0 mmol) of Boc-anhydride. The resulting solution was stirred overnight at ambient temperature then concentrated to dryness. The residue was dissolved in water, washed with ether and acidified to pH=2 with 5N HCl. The acidic aqueous layer was extracted with 20% isopropanol/chloroform. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness to yield 3.2 g (86%) of the desired mixture of isomers as a white solid. MS (ion spray) 228.2 (M−1).

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ether
  4. extractionThe acidic aqueous layer was extracted with 20% isopropanol/chloroform
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bbf08d8c1c984db9a178426fd233220d
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

Loading…