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

HRID 427714Notes

Reaction equation

HRID 427714 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH2:9]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 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 1-Boc-4-methoxycarbonyl-3,4-didehydropiperidine (28.81 g, 119 mmol) in methanol (300 mL) was added 1 N aqueous sodium hydroxide (300 mL). After stirring overnight, the solvent was removed by rotary evaporation and the residue was partitioned between water and diethyl ether. The aqueous phase was separated and washed with diethyl ether, acidified to pH 2.5 with conc. HCl, then extracted with diethyl ether. The organic extract was then washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 25.16 g (93%) of a light yellow solid.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customthe residue was partitioned between water and diethyl ether
  3. customThe aqueous phase was separated
  4. washwashed with diethyl ether
  5. extractionextracted with diethyl ether
  6. extractionThe organic extract
  7. washwas then washed with brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6b8d167a4e9418cac8500d4c8df2e62
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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