Sodium hydride → HCID 18978687, compound

HRID 1507251Notes

Reaction equation

HRID 1507251 reaction equation
[Br:1][CH:2]([CH2:17][CH2:18]Br)[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=[O:4].[H-].[Na+]>O1CCCC1.O>[Br:1][CH:2]1[CH2:17][CH2:18][N:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:3]1=[O:4]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 18978654HCID 18978654, compound

Product 1

HCID 18978687HCID 18978687, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2,4-dibromo-N-(4-(trifluoromethyl)benzyl)butanamide (6.8 g, 16.9 mmol) in tetrahydrofuran (200 mL) was added NaH (1.35 g, 34 mmol) and the reaction was stirred at rt for 4 h. The reaction mixture was then diluted with water and twice extracted with 30 mL of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by silica gel chromatography eluting with 0-40% ethyl acetate/hexanes to afford 2.8 g of 3-bromo-1-(4-(trifluoromethyl)benzyl)pyrrolidin-2-one (48%). LCMS (method Q) RT 0.90 min, m/z 322.1 (M+H+; 1H NMR (400 MHz, chloroform-d) δ 12.39 (d, J=8.0 Hz, 2H), 12.16 (d, J=8.0 Hz, 2H), 9.46-9.38 (m, 1H), 9.25 (d, J=1.8 Hz, 2H), 8.27-8.17 (m, 1H), 7.99 (s, 1H), 7.43-7.31 (m, 1H), 7.14-7.05 (m, 1H).

Workup

  1. extractiontwice extracted with 30 mL of ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f868dd56591a443285203a7db84471a7
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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