Sodium hydride → 2-Benzyl-2-azaspiro[4.4]nonane-1,4-dione

HRID 1477943Notes

Reaction equation

HRID 1477943 reaction equation
[H-].[Na+].[CH2:3]([NH:10][C:11]([C:13]1([C:18](=[O:21])[CH2:19]Br)[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C=O)C>[CH2:3]([N:10]1[CH2:19][C:18](=[O:21])[C:13]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[C:11]1=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 10639676N-benzyl-1-(2-bromoacetyl)cyclopentanecarboxamide

Product 1

HCID 107053912-Benzyl-2-azaspiro[4.4]nonane-1,4-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (60% mineral oil suspension, 7.40 g, 185.00 mmol) in DMF (450 mL) was added a solution of N-benzyl-1-(2-bromoacetyl)cyclopentanecarboxamide (50.00 g, 154.22 mmol) in DMF (100 mL) dropwise at 0° C. After addition, the reaction mixture was stirred at rt overnight and then quenched with water (200 mL) and extracted with EtOAc (300 mL×3). The combined organic phases were washed with brine (300 mL×3), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10) to give the product as yellow oil (21.00 g, 56.0%).

Workup

  1. additionAfter addition
  2. customquenched with water (200 mL)
  3. extractionextracted with EtOAc (300 mL×3)
  4. washThe combined organic phases were washed with brine (300 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10)

Sources & evidence

ORD record
ord-b6a85910dfb94d728a6f04fe4a60cffc
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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