乙酸乙酯 → 5-(5-Bromo-3-pyridinyl)-1-methyl-2-pyrrolidinone

HRID 1044

反应方程式

HRID 1044 反应方程式
[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

参与物

6

反应物 4

HCID 8857乙酸乙酯HCID 4311764硼氢化钠HCID 6327182碲HCID 196943305-Bromo-3-(3,3-dibromo-1-methyl-5-pyrrolidin-2-onyl)pyridine

产物 1

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

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-90e66e44000e45b397f6a1aa0fe837fd
来源数据集
uspto-grants-1998_03
专利号
US05723477

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