Hydrochloric Acid → [1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acid

HRID 1004506Notes

Reaction equation

HRID 1004506 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>CO.O>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:19])=[O:3])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetate

Product 1

HCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound (5.28 g) obtained in the above (1) is dissolved in methanol (32 ml), and thereto is added 1N aqueous sodium hydroxide solution (23.4 ml), and the mixture is stirred at room temperature for three hours. The reaction mixture is diluted with water, and the pH value thereof is adjusted to pH 2 with 1N hydrochloric acid, and extracted three time with ethyl acetate. The extract is washed twice with a saturated brine, and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (5.18 g).

Workup

  1. extractionextracted three time with ethyl acetate
  2. washThe extract is washed twice with a saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccant is removed by filtration
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-df2746bd773e4f74aa6a4e47e5fc6a29
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

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