Water → 4-Methyl-3-oxo-piperidine-1-carboxylic Acid Methyl Ester

HRID 7215Notes

Reaction equation

HRID 7215 reaction equation
O.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH3:13][O:14][C:15]([N:17]1[CH:22]=[C:21]([O:23]C(=O)C)[CH:20]([CH3:27])[CH2:19][CH2:18]1)=[O:16]>CO>[CH3:13][O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([CH3:27])[C:21](=[O:23])[CH2:22]1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 69656130HCID 69656130, compound

Product 1

HCID 451228894-Methyl-3-oxo-piperidine-1-carboxylic Acid Methyl EsterYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

In a 1000 ml round bottom flask, 50 g of crude 5-acetoxy-4-methyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester was dissolved in 200 ml of methanol. To 300 ml water was added 30 g of sodium carbonate and 30 g sodium bicarbonate (pH=10). The aqueous buffer was added to the methanol solution. Methanol was added to the mixture until it stirred easily, and stirred at room temperature for 18 hours. The mixture was then concentrated to remove methanol. Water was added to the mixture to dissolve all salts. This was then extracted with ethyl acetate three times. The organic extracts were combined, dried over magnesium sulfate, filtered, and evaporated to furnish the crude compound 4-Methyl-3-oxo-piperidine-1-carboxylic acid methyl ester as oil, which was then purified as described below.

Workup

  1. stirringstirred at room temperature for 18 hours
  2. concentrationThe mixture was then concentrated
  3. customto remove methanol
  4. additionWater was added to the mixture
  5. dissolutionto dissolve all salts
  6. extractionThis was then extracted with ethyl acetate three times
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-dd36c0ffd6af4bbb82b6d263461c6525
Source dataset
uspto-grants-2006_08
Patent number
US07084277B2

Reaction notes

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