Sodium Carbonate → 1-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

HRID 1436866ノート

反応式

HRID 1436866 の反応式
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9](S(C3C=CC=CC=3)=O)[C:8]2=[O:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:21])=[CH:22][CH:23]=1

参加物

4

反応物 2

HCID 10340Sodium CarbonateHCID 690624651-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

生成物 1

HCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a stirred solution of 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one one (25 g, 74 mmol) in toluene (200 mL) was added anhydrous sodium carbonate (20 g, 190 mmol). The mixture was heated to reflux for 1.5 hours. The reaction mixture was cooled to ambient temperature and the solids were removed by filtration. The filtrate solvent was removed under vacuum and the residue was purified using silica gel column chromatography eluting with 3:1 EtOAc:hexanes. Appropriate fractions were combined and removal of the solvents under vacuum gave the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.01 (m, 2H), 6.56 (dt, J=9.9, 4.2 Hz, 1H), 6.00 (dt, J=9.7, 1.8 Hz, 1H), 4.59 (s, 2H), 3.32 (t, J=7.2 Hz, 2H), 2.33 (m, 2H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. customthe solids were removed by filtration
  4. customThe filtrate solvent was removed under vacuum
  5. customthe residue was purified
  6. washeluting with 3:1 EtOAc
  7. customremoval of the solvents under vacuum

出典と根拠

ORDレコード
ord-d39c92291ee846b59b3c756bad62b4bc
出典データセット
uspto-grants-2009_11
特許番号
US07619086B2

反応ノート

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