Sodium → Methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylate
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.