Ethyl bromoacetate → Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetate

HRID 1667122ノート

反応式

HRID 1667122 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:9]2=[O:13])=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 673585653,3-Bis(4-fluorophenyl)pyrrolidin-2-one

生成物 1

HCID 67358887Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of the product from Example 58B (0.82 g, 3.00 mmol) in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran, 4.5 mL, 4.5 mmol) via syringe under nitrogen followed by ethyl 2-bromoacetate (0.33 mL, 3.00 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated and then diluted with ethyl acetate. The reaction mixture was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified with silica gel chromatography eluting with ethyl acetate/hexane (20:80) gave the title compound. MS (APCI+) m/z 359.9 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washThe reaction mixture was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel chromatography
  9. washeluting with ethyl acetate/hexane (20:80)

出典と根拠

ORDレコード
ord-ddedb08011fb42c98960fdd27a629f3b
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

反応ノート

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