Lithium Hydroxide → 1-(Cyclopentylcarbonyl)-5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylic acid

HRID 1642791Notes

Reaction equation

HRID 1642791 reaction equation
O1CCOCC1.[OH-].[Li+].[CH:9]1([C:14]([N:16]2[CH2:21][CH:20]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[CH2:19][CH:18]([C:31]([O:33]CC)=[O:32])[CH2:17]2)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1>O>[CH:9]1([C:14]([N:16]2[CH2:21][CH:20]([C:22]3[CH:23]=[CH:24][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:26][CH:27]=3)[CH2:19][CH:18]([C:31]([OH:33])=[O:32])[CH2:17]2)=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 58002165Ethyl 1-(cyclopentylcarbonyl)-5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylate

Product 1

HCID 580024031-(Cyclopentylcarbonyl)-5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of dioxane, 25 ml of water and 0.63 g (25.8 mmol) of lithium hydroxide were added to 2.40 g (6.46 mmol) of ethyl 1-(cyclopentylcarbonyl)-5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylate. The mixture was stirred at RT overnight. For work-up, the dioxane was removed under reduced pressure, water was added to the reaction mixture and the mixture was acidified using aqueous 1 N hydrochloric acid solution. The mixture was extracted with dichloromethane. The organic phase was dried with sodium sulphate and concentrated under reduced pressure. Yield: 1.65 g (98% of theory)

Workup

  1. customFor work-up, the dioxane was removed under reduced pressure, water
  2. additionwas added to the reaction mixture
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0ef5cdd87d04659abda9e8708fda9b3
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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