Sodium → Ethyl 2,4-dioxo-5-phenylpiperidine-3-carboxylate

HRID 1180089Notes

Reaction equation

HRID 1180089 reaction equation
[Na].C(O[C:5](=[O:23])[CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])C>C(O)C.C1(C)C=CC=CC=1>[O:16]=[C:9]1[CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5](=[O:23])[CH:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:7][NH:8]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 251937233-(2-Ethoxycarbonyl-acetylamino)-2-phenyl-propionic acid ethyl ester

Product 1

HCID 25193512Ethyl 2,4-dioxo-5-phenylpiperidine-3-carboxylateYield 48.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Sodium (380 mg, 16.52 mmol) was dissolved in anhydrous ethanol (13 mL) and the resulting solution was treated dropwise with 3-(2-ethoxycarbonyl-acetylamino)-2-phenyl-propionic acid ethyl ester (4.23 g, 13.76 mmol) dissolved in anhydrous toluene (35 mL). The reaction was kept at 80° C. for 1.5 hours. After cooling, the mixture was extracted with water. The aqueous extracts were acidified with 2 N HCl, extracted with ethyl acetate and the organic layers were collected, dried over Na2SO4 and evaporated to dryness to obtain ethyl 2,4-dioxo-5-phenylpiperidine-3-carboxylate (1.73 g, Y=48%) which was used for the next step without further purification. Ethyl 2,4-dioxo-5-phenylpiperidine-3-carboxylate (1.73 g, 6.63 mmol) was dissolved in acetonitrile containing 1% of water (30 mL) and the resulting solution was refluxed for 2 hours. After evaporating to dryness, the crude material was chromatographed on silica gel, eluting with methylene chloride/methanol 92/8, to give the title compound (780 mg, Y=62%) as a solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with water
  3. extractionextracted with ethyl acetate
  4. customthe organic layers were collected
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-24a039dfe07446e7a34901f2acb43407
Source dataset
uspto-grants-2007_10
Patent number
US07279575B2

Reaction notes

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