Lithium Hydroxide → 4-(1-Tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetic acid

HRID 412612Notes

Reaction equation

HRID 412612 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Li+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:26][CH:27]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 18536423HCID 18536423, compound

Product 1

HCID 185363314-(1-Tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetic acidYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(1-tert-butoxycarbonylpiperidin4-yloxy)-phenoxyacetate (23.71 g) in a mire of tetrahydrofuran (34 ml) and ethanol (34 ml) was dropwise added 1N aqueous lithium hydroxide solution (68.7 ml) with ice-cooling, and the mixture was stirred at room temperature for 20 min. After completion of the reaction, the solvent was evaporated and to the obtained residue was added 10% aqueous citric acid solution. The mixture was extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The obtained solid was filtrated with hexane and dried under reduced pressure to give the title compound (19.09 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated and to the obtained residue
  4. additionwas added 10% aqueous citric acid solution
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed successively with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. filtrationThe obtained solid was filtrated with hexane
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f9386a9073b9493ca22955fdad5c6853
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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