Lithium Hydroxide → 5-(4-Ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid

HRID 1642814Notes

Reaction equation

HRID 1642814 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24]([O:26]CC)=[O:25])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Li+]>O1CCOCC1.O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24]([OH:26])=[O:25])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58002667Ethyl 5-(4-ethylphenyl)1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 580026415-(4-Ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

880 mg (2.24 mmol) of ethyl 5-(4-ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylate were dissolved in a mixture of 15.5 ml of dioxane and 7.7 ml of water, 215 mg (8.97 mmol) of lithium hydroxide were added and the mixture was stirred at RT overnight. For work-up, the reaction solution was concentrated under reduced pressure, water was then added and the mixture was acidified with 1N hydrochloric acid. The precipitate formed was filtered off and dried under reduced pressure. The filtrate was extracted with ethyl acetate. The combined organic phases were dried with sodium sulphate and concentrated under reduced pressure. The two solids gave a total yield of 764 mg (95% of theory).

Workup

  1. additionwere added
  2. concentrationFor work-up, the reaction solution was concentrated under reduced pressure, water
  3. additionwas then added
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customdried under reduced pressure
  7. extractionThe filtrate was extracted with ethyl acetate
  8. dry with materialThe combined organic phases were dried with sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe two solids gave a total yield of 764 mg (95% of theory)

Sources & evidence

ORD record
ord-561511a93c794124ae753bdb05983954
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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