Sodium hydride → Ethyl 2-(3-bromo-2-oxopyrrolidin-1-yl)acetate

HRID 1752253Notes

Reaction equation

HRID 1752253 reaction equation
[Br:1][CH:2]([CH2:12][CH2:13]Br)[C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[H-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][CH:2]1[CH2:12][CH2:13][N:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]1=[O:4]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 54371553Ethyl 2-(2,4-dibromobutanamido)acetate

Product 1

HCID 14257595Ethyl 2-(3-bromo-2-oxopyrrolidin-1-yl)acetateYield 24.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of crude ethyl 2-(2,4-dibromobutanamido)acetate (2.847 g, 8.60 mmol) in benzene (8.6 mL) at 5° C. was added portionwise a 60% mineral oil dispersion (344 mg) of sodium hydride (206 mg, 8.60 mmol) over 20 minutes. The reaction was stirred an additional 10 minutes before being poured onto ice water and diluted with ethyl acetate. The layers were separated. The organic phase was brine-washed, dried over sodium sulfate, filtered, concentrated down, and dried. The mixture of starting dibromide and product was purified by eluting through a silica gel column with a 0 to 100% ethyl acetate/heptane gradient to afford the title racemic compound (523 mg, 24% yield) as a clear oil. MS (ESI) [m/e, (M+H)+]=251.5. 1H NMR (400 MHz, chloroform-d) δ ppm 4.46 (dd, J=7.07, 3.03 Hz, 1H), 3.96-4.28 (m, 4H), 3.63-3.72 (m, 1H), 3.43-3.53 (m, 1H), 2.63-2.76 (m, 1H), 2.34-2.43 (m, 1H), 1.26-1.34 (m, 3H).

Workup

  1. additionbefore being poured onto ice water
  2. customThe layers were separated
  3. washwashed
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customdried
  8. additionThe mixture of starting dibromide and product
  9. customwas purified
  10. washby eluting through a silica gel column with a 0 to 100% ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-14324a74ac3e4ab7a43df78d8ed87708
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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