Hydrochloric Acid → 1-[1,2-Dioxo-2-(thien-2-yl)ethyl)-2-piperidinecarboxylic acid

HRID 7904Notes

Reaction equation

HRID 7904 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]1[S:5][CH:6]=[CH:7][CH:8]=1.[Li+].[OH-].Cl>CO>[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]1[S:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21992934Methyl 1-[1,2-Dioxo-2-(thien-2-yl)ethyl)-2-piperidinecarboxylate

Product 1

HCID 98168041-[1,2-Dioxo-2-(thien-2-yl)ethyl)-2-piperidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 2 (2.45 g, 8.72 mmol) was dissolved in MeOH (50 mL). LiOH solution (1 N, 13 mL) was added at 0° C., and the mixture was stirred at the same temperature for 2 h and at room temperature for 16 h. The reaction mixture was acidified with 1 N HCl, and extracted with ethyl acetate. The organic phase was washed with brine and dried with MgSO4. After evaporation of the solvent and drying under vacuum, a yellow solid was obtained, and was used for the next step without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with MgSO4
  4. customAfter evaporation of the solvent
  5. customdrying under vacuum
  6. customa yellow solid was obtained
  7. customwas used for the next step without purification

Sources & evidence

ORD record
ord-46f3493837464fa1985f3dcce3aef5a5
Source dataset
uspto-grants-2006_08
Patent number
US07087628B2

Reaction notes

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