Sodium hydride → (+/-)-tert-Butyl (2a-methyl-2,4-dioxo-2a,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-1(2H)-yl)acetate

HRID 641446Notes

Reaction equation

HRID 641446 reaction equation
[H-].[Na+].[CH3:3][C:4]12[C:15](=[O:16])[NH:14][C:12]3[C:13]1=[C:8]([CH:9]=[CH:10][CH:11]=3)[NH:7][C:6](=[O:17])[CH2:5]2.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C>[CH3:3][C:4]12[C:15](=[O:16])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]3[C:13]1=[C:8]([CH:9]=[CH:10][CH:11]=3)[NH:7][C:6](=[O:17])[CH2:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 576637492a-Methyl-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione

Product 1

HCID 86642130(+/-)-tert-Butyl (2a-methyl-2,4-dioxo-2a,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-1(2H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (71 mg of a 60% dispersion in mineral oil, 1.78 mmol) was added to a solution of (±)-2a-methyl-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione from Step C (298 mg, 1.47 mmol) in DMF (3 mL) at 0° C. After 1 h, tert-butyl bromoacetate (0.219 mL, 1.48 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was quenched with H2O (5 mL) and extracted with CH2Cl2 (3×10 mL) then EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=317 (M+1).

Workup

  1. customThe reaction mixture was quenched with H2O (5 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-e1e48ca7049148d2aaffa16924dfc2f7
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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