Ethyl Acetate → 5-(5-Bromo-3-pyridinyl)-1-methyl-2-pyrrolidinone

HRID 1489407

반응식

HRID 1489407 반응식
[BH4-].[Na+].[Te].[Br:4][C:5]1[CH:6]=[C:7]([CH:11]2[N:15]([CH3:16])[C:14](=[O:17])[C:13](Br)(Br)[CH2:12]2)[CH:8]=[N:9][CH:10]=1.C(OCC)(=O)C>C(O)C>[Br:4][C:5]1[CH:6]=[C:7]([CH:11]2[N:15]([CH3:16])[C:14](=[O:17])[CH2:13][CH2:12]2)[CH:8]=[N:9][CH:10]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 196943305-Bromo-3-(3,3-dibromo-1-methyl-5-pyrrolidin-2-onyl)pyridine

생성물 1

HCID 196943295-(5-Bromo-3-pyridinyl)-1-methyl-2-pyrrolidinone수율 68%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium borohydride (862 mg, 22.8 mmol) was dissolved in ethanol (20 mL) and tellurium metal powder (1.45 g, 11.4 mmol) was added in portions. The mixture was heated under reflux for 0.25 h and 5-bromo-3-(3,3-dibromo-1-methyl-5-pyrrolidin-2-onyl)pyridine (775 mg, 1.9 mmol) was added to the solution at 25° C. After stirring for 2 h, ethyl acetate (50 mL) was added and the solution was filtered through Celite and concentrated in vacuo. 1M HCl (10 mL) was added to the residue and the solution was adjusted to pH 11 with solid potassium carbonate. After extraction with ethyl acetate (50 mL) the organic phase was separated. The aqueous phase was extracted with ethyl acetate (2×50 mL) and the combined organic phases were washed with brine (30 mL), dried (MgSO4) and concentrated. This material was chromatographed on silica gel with ethyl acetate:hexane (1:1) as eluant to afford 5-bromo-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine as a solid (329 mg, 68%). M.p. 85°-87° C.; 1H NMR (CDCl3, 300 MHz): δ 8.66 (d, J=2 Hz, 1H), 8.42 (d, J=2 Hz, 1H), 7.68 (t, J=2 Hz, 1H), 4.56 (t, J=7 Hz, 1H), 2.71 (s, 3H), 2.45-2.65 (m, 2H), 1.80-1.95 (m, 2H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 0.25 h
  3. filtrationthe solution was filtered through Celite
  4. concentrationconcentrated in vacuo
  5. addition1M HCl (10 mL) was added to the residue
  6. extractionAfter extraction with ethyl acetate (50 mL) the organic phase
  7. customwas separated
  8. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  9. washthe combined organic phases were washed with brine (30 mL)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThis material was chromatographed on silica gel with ethyl acetate:hexane (1:1) as eluant

출처 및 근거

ORD 기록
ord-bd5df2351f7d43408353da845f00aa80
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677459

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