Potassium Carbonate → 1-[(4-Fluorophenyl)methyl]pyrrolidine-2,5-dione

HRID 853615노트

반응식

HRID 853615 반응식
C(=O)([O-])[O-].[K+].[K+].[C:7]1(=[O:13])[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>CC(C)=O>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:11]2[C:10](=[O:12])[CH2:9][CH2:8][C:7]2=[O:13])=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 11439SuccinimideHCID 680214-Fluorobenzyl bromide

생성물 1

HCID 225103401-[(4-Fluorophenyl)methyl]pyrrolidine-2,5-dione수율 85.1%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Freshly ground potassium carbonate, K2CO3 (31 g, 225 mmol) was added to dry acetone (200 ml) in a 3-necked flask equipped with drying tube, condenser, and mechanical stirrer. Succinimide (7.43 g, 75 mmol) and 4-fluorobenzylbromide (11.21 mL, 90 mmol) were added. The mixture was refluxed for 19 hours and filtered through Celite. Acetone was removed under vacuum, diluted with EtOAc, washed with saturated aqueous sodium bicarbonate and also with brine, dried (MgSO4), filtered and concentrated to give crude. Crude product was chromatographed (EtOAc/Hexane) on silica gel to give N-4-fluorobenzyl-succinimide 1 as white solid (13.22 g, 85%). 1H NMR (CDCl3) δ 7.4 (dd, 2H), 7.0 (t, 2H), 4.6 (s, 1H), 2.7 (s, 4 H).

후처리

  1. customequipped
  2. customwith drying tube, condenser, and mechanical stirrer
  3. temperatureThe mixture was refluxed for 19 hours
  4. filtrationfiltered through Celite
  5. customAcetone was removed under vacuum
  6. additiondiluted with EtOAc
  7. washwashed with saturated aqueous sodium bicarbonate and also with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give crude
  12. customCrude product was chromatographed (EtOAc/Hexane) on silica gel

출처 및 근거

ORD 기록
ord-2261eb272a7347afa437919af31d1ef7
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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