Sodium → Methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylate

HRID 1196417Notes

Reaction equation

HRID 1196417 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]([NH:9][C:10]([CH3:17])([CH3:16])[CH2:11][C:12]([O:14]C)=O)=[O:8])=[O:5])C.[Na]>CO>[CH3:16][C:10]1([CH3:17])[NH:9][C:7](=[O:8])[CH:6]([C:4]([O:3][CH3:1])=[O:5])[C:12](=[O:14])[CH2:11]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 53932766Methyl 3-(ethoxycarbonylacetamido)-3-methylbutyrate

Product 1

HCID 19898238Methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-(ethoxycarbonylacetamido)-3-methylbutyrate (45 g) and sodium metal (4.22 g) in anhydrous methanol (450 ml) was heated at a reflux for 3 hours. The cooled mixture was evaporated under reduced pressure and the residue dissolved in water (200 ml). The aqueous solution was washed with ether (3×100 ml), acidified with 2N hydrochloric acid and the acidic mixture extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (2×100 ml), dried over magnesium sulphate and evaporated under reduced pressure to give methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylate (26.3 g), mp 170°-172° C., as a cream crystalline solid.

Workup

  1. temperaturea reflux for 3 hours
  2. customThe cooled mixture was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in water (200 ml)
  4. washThe aqueous solution was washed with ether (3×100 ml)
  5. extractionthe acidic mixture extracted with dichloromethane (3×100 ml)
  6. washThe combined extracts were washed with water (2×100 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-555f8bf24c7c45ce842095d084cedf83
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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