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

HRID 496080Notes

Reaction equation

HRID 496080 reaction equation
[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([O:18]C)=[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 22257833Methyl 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylate

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 methyl 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylate (3.30 g; 12.25 mmol), 1 N LiOH (15 ml), and methanol (60 ml) was stirred at 0° C. for 30 minutes and at room temperature overnight. The mixture was acidified to pH 1 with 1 N HCl, diluted with water, and extracted into 100 ml of methylene chloride. The organic extract was washed with brine and concentrated to deliver 2.80 g (87%) of snow-white solid which did not require further purification. 1H NMR (CDCl3): δ 0.89 (t, 3H); 1.21, 1.24 (s, 3H each); 1.42-1.85 (m, 7H); 2.35 (m, 1H) 3.22 (d, 1H); 3.42 (m, 1H); 5.31 (d, 1H).

Workup

  1. extractionextracted into 100 ml of methylene chloride
  2. extractionThe organic extract
  3. washwas washed with brine
  4. concentrationconcentrated
  5. custompurification

Sources & evidence

ORD record
ord-d7ce4ce329e642fe96565a2fe3185f9e
Source dataset
uspto-grants-2005_09
Patent number
US06943187B2

Reaction notes

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