Ethyl bromoacetate → HCID 10568063, compound

HRID 492234Notes

Reaction equation

HRID 492234 reaction equation
[CH2:1]([N:8]1[CH:16]([OH:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:18][CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[N:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 32407432-benzyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 10568063HCID 10568063, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 20 (2.0 g, 8.4 mmol) in DMF (28 mL) at room temperature was added sodium hydride (235 mg, 8.8 mmol) and ethyl bromoacetate (1.03 mL, 9.2 mmol) and the resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture is poured onto water and extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to provide 2 g of 21 as a clear oil (2.73 g theoretical, 73% yield)

Workup

  1. customthe resulting reaction mixture
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38fb03222e0e4663bb5f35533d62ecd8
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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