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

HRID 1642815Notes

Reaction equation

HRID 1642815 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]([C:23]#[N:24])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:25]([O:27]CC)=[O:26])[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]([C:23]#[N:24])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:25]([OH:27])=[O:26])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58002479Ethyl 5-(4-ethylphenyl)-1-[(4-cyanopiperidin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 580024245-(4-Ethylphenyl)-1-[(4-cyanopiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

650 mg (1.60 mmol) of ethyl 5-(4-ethylphenyl)-1-[(4-cyanopiperidin-1-yl)carbonyl]piperidine-3-carboxylate were dissolved in a mixture of 20 ml of dioxane and 10 ml of water, 153 mg (6.40 mmol) of lithium hydroxide were added and the mixture was stirred at RT for 15 min. 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 residue was purified by preparative HPLC. Yield: 347 mg (59% 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. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-19eb030537df45219aa08c02d0d234d5
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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