Hydrochloric Acid → 1-(3,3-Dimethyl-2-oxopentanoyl)piperidine-2-carboxylic acid

HRID 1828059Notes

Reaction equation

HRID 1828059 reaction equation
[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([O:18]CC)=[O:17])[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][CH3:6].[Li+].[OH-].CO.Cl>O>[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([OH:18])=[O:17])[C:3](=[O:9])[C:4]([CH3:7])([CH3:8])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 9903902Ethyl 1-(3,3-dimethyl-2-oxo-pentanoyl)piperidine-2-carboxylate

Product 1

HCID 220647601-(3,3-Dimethyl-2-oxopentanoyl)piperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylate (0.69 g; 2.43 mmol), 1 N LiOH (5 mL), and methanol (20 mL) was stirred at 0° C. for 30 min and at room temperature overnight. The mixture was acidified to pH 1 with 1 N HCl, diluted with water, and extracted into 50 mL of methylene chloride. The organic extract was washed with brine and concentrated to deliver 0.61 g (98%) of snow-white solid which did not require further purification.

Workup

  1. extractionextracted into 50 mL of methylene chloride
  2. extractionThe organic extract
  3. washwas washed with brine
  4. concentrationconcentrated
  5. custompurification

Sources & evidence

ORD record
ord-e3a78643581b4116bfe2775b51f151e7
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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