Sodium hydride → HCID 68777402, compound

HRID 2061576Notes

Reaction equation

HRID 2061576 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Cl)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 68779529HCID 68779529, compound

Product 1

HCID 68777402HCID 68777402, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The ester compound in dry THF (15 mL) was added to a suspension of NaH (352 mgs, 8.81 mmol) in dry THF (3 mL) and stirred at room temperature for 16 hours. The reaction mixture was then quenched with water (4 mL), diluted with ethyl acetate (60 mL), dried over MgSO4, filtered, and purified by flash chromatography on silica gel with stepwise elution using 50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gave 4-(2-oxo-pyrrolidin-1-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.28 g, 58.0% yield).

Workup

  1. customThe reaction mixture was then quenched with water (4 mL)
  2. additiondiluted with ethyl acetate (60 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. custompurified by flash chromatography on silica gel with stepwise elution

Sources & evidence

ORD record
ord-c643e9e54fac44a0aeac1d55f6b734aa
Source dataset
uspto-grants-2012_10
Patent number
US08283357B2

Reaction notes

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