Sodium hydride → HCID 178501171, compound

HRID 491826Notes

Reaction equation

HRID 491826 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1)=[O:8].[Cl-].[NH4+]>CN(C)C(=O)C>[O:8]=[C:7]1[CH2:6][CH2:5][CH2:4][N:9]1[C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178501233HCID 178501233, compound

Product 1

HCID 178501171HCID 178501171, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sixty % sodium hydride in oil (9.60 g) is suspended in N,N-dimethyacetamide (500 ml), to this mixture is added methyl trans-4-(4-chlorobutyrylamino)-cyclohexanecarboxylate (52.32 g) obtained in Reference Example 113(2) gradually under ice-cooling. The reaction solution is warmed to room temperature, stirred for 24 hours, and thereto are poured saturated aqueous ammonium chloride solution and ice-water, and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: ethyl acetate) and the obtained solid is suspended in n-hexane-diisopropyl ether. The resulting crystals are collected by filtration and dried to give methyl trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylate (39.20 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (eluent: ethyl acetate)
  8. filtrationThe resulting crystals are collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-119e0c7446f9429381125f434892c627
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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