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

HRID 661206Notes

Reaction equation

HRID 661206 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 workup, the reaction solution was concentrated under reduced pressure, then water was added and the mixture was acidified with 1N hydrochloric acid. The precipitate formed was filtered off, washed and dried under reduced pressure. The filtrate was extracted with ethyl acetate. The combined organic phases were dried over 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 workup, the reaction solution was concentrated under reduced pressure
  3. additionwater was added
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed
  7. customdried under reduced pressure
  8. extractionThe filtrate was extracted with ethyl acetate
  9. dry with materialThe combined organic phases were dried over sodium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customThe two solids gave a total yield of 764 mg (95% of theory)

Sources & evidence

ORD record
ord-c603f349456740768e95e1250a26a970
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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