Sodium hydride → HCID 86742163, compound

HRID 1252510Notes

Reaction equation

HRID 1252510 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C:17]([O:19]C)=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7].[H-].[Na+]>O1CCOCC1>[O:19]=[C:17]1[CH:4]([C:3]([O:2][CH3:1])=[O:21])[CH2:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 73943104HCID 73943104, compound

Product 1

HCID 86742163HCID 86742163, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(4-Methoxy-1,4-dioxobutyl)-L-phenylalanine, methyl ester, 6.74 g (0.023 mole), was dissolved in 200 ml of dioxane, and 2.2 g (0.055 mole) of 60% sodium hydride in mineral oil dispersion slowly added. The mixture was refluxed for four hours, stirred, and allowed to reach room temperature overnight. The solvent was evaporated in vacuo and the residue dissolved in 100 ml of water, acidified with concentrated hydrochloric acid to pH 8.5 and extracted with 200 ml ethyl acetate. The ethyl acetate layer was separated, dried over sodium sulfate, evaporated in vacuo, and the residue chromatographed using 150 g of silica gel and eluting with 500 ml of dichloromethane-methanol (98:2) to give 3,6-dioxo-2-(phenylmethyl)-4-piperidinecarboxylic acid, methyl ester: (DL-mixture at 2 position), 5.1 g; mp 146°-147.5°.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in 100 ml of water
  4. extractionextracted with 200 ml ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customthe residue chromatographed
  9. washeluting with 500 ml of dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-ba6d3cfb071649cf88ff021f628bdced
Source dataset
uspto-grants-1988_05
Patent number
US04743585

Reaction notes

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