Sodium Hydroxide → 1-((Tert-butoxy)carbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylic acid

HRID 988604Notes

Reaction equation

HRID 988604 reaction equation
[C:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118067821-Tert-butyl 4-methyl 1,2,3,6-tetrahydropyridine-1,4-dicarboxylate

Product 1

HCID 177817901-((Tert-butoxy)carbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 1-Boc-1,2,3,6-tetrahydro-4-pyridinecarboxylate (2.22 g, 9.2 mmol) in methanol (10 mL) was added 1.0 N aqueous sodium hydroxide (25 mL). After stirring for 2 h, the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water, and the layers were separated. The aqueous phase was acidified to pH 2.5 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 1.62 g (78%) of the title compound as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between diethyl ether and water
  3. customthe layers were separated
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with saturated aqueous sodium chloride
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ad117e5192c469eac24d007bfc35d09
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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