Sodium hydride → HCID 59075084, compound

HRID 2184331Notes

Reaction equation

HRID 2184331 reaction equation
[H-].[Na+].COP([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)=[O:11])(=O)OC.[CH3:19][O:20][C:21](=[O:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C@@H:29]1[CH:34]=O>COCCOC>[CH3:19][O:20][C:21](=[O:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C@@H:29]1/[CH:34]=[CH:9]/[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20792907HCID 20792907, compoundHCID 59075104Methyl 7-[(2R)-2-formyl-5-oxopyrrolidin-1-yl]heptanoate

Product 1

HCID 59075084HCID 59075084, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of NaH (0.14 g, 1 eq) in 30 mL of ethylene glycol dimethyl ether stirred at 0° C. under nitrogen was added [2-(3-bromo-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester (1.82 g, 1.05 eq). After 1 hour at 0° C., 7-((R)-2-formyl-5-oxo-pyrrolidin-1-yl)-heptanoic acid methyl ester (1.44 g, 5.64 mmol) in 2 mL of DME was added slowly. The ice bath was removed and then the mixture was stirred for an additional 3 hours at room temperature. Saturated ammonium chloride solution was added and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by chromatography. EtOAc(1):Hexane(1)followed by EtOAc(5):Hexane(1) to yield 1.6 g of 7-{(R)-2-[(E)-3-(3-bromo-phenyl)-3-oxo-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid methyl ester.

Workup

  1. customThe ice bath was removed
  2. additionSaturated ammonium chloride solution was added
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-0160bad55c824353a02b69f2bc42e725
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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