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

HRID 853615ノート

反応式

HRID 853615 の反応式
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

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 11439SuccinimideHCID 680214-Fluorobenzyl bromide

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2261eb272a7347afa437919af31d1ef7
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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