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Water → (E)-4-(3,5-bis(trifluoromethyl)phenyl)-1-(3-(3,3-difluoroazetidin-1-yl)-3-oxoprop-1-enyl)pyrrolidin-2-one

HRID 1486991
ノート
印刷プレビュー

反応式

HRID 1486991 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[F:23][C:24]1([F:33])[CH2:27][N:26]([C:28](=[O:32])/[CH:29]=[CH:30]\I)[CH2:25]1.O>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:7]1[CH:6]=[C:5]([CH:13]2[CH2:17][N:16](/[CH:30]=[CH:29]/[C:28]([N:26]3[CH2:27][C:24]([F:33])([F:23])[CH2:25]3)=[O:32])[C:15](=[O:18])[CH2:14]2)[CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 816553704-(3,5-Bis(trifluoromethyl)phenyl)pyrrolidin-2-oneHCID 86730374(Z)-1-(3,3-difluoroazetidin-1-yl)-3-iodoprop-2-en-1-one

生成物 1

HCID 86298784(E)-4-(3,5-bis(trifluoromethyl)phenyl)-1-(3-(3,3-difluoroazetidin-1-yl)-3-oxoprop-1-enyl)pyrrolidin-2-one収率 4.03%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

4-(3,5-bis(trifluoromethyl)phenyl)pyrrolidin-2-one (0.5 g, 1.0 eq.) was dissolved in DMF (5 mL) and cooled to 0° C. A solution of NaH in DMF (0.133 g, 2.0 eq.) was added at 0° C. (Z)-1-(3,3-difluoroazetidin-1-yl)-3-iodoprop-2-en-1-one (0.689 g, 1.5 eq.) was then introduced. The reaction mixture was stirred for 30 min at room temp. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (3×50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 0.502 g of crude product, which was purified by chromatography (1% Methanol in DCM) to give 0.030 g of (E)-4-(3,5-bis(trifluoromethyl)phenyl)-1-(3-(3,3-difluoroazetidin-1-yl)-3-oxoprop-1-enyl)pyrrolidin-2-one (Yield 4.03%). 1H NMR (400 MHz, CDCl3) δ 8.15-8.19 (d, J=14 Hz, 1H), 7.69-7.87 (m, 3H), 5.27-5.31 (d, J=14 Hz, 1H), 4.05-4.47 (m, 4H), 3.89-3.93 (s, 1H), 3.73-3.77 (s, 1H), 3.60-3.62 (s, 1H), 3.08-3.13 (s, 1H), 2.78-2.90 (s, 1H); LCMS calcd. for C18H14F8N2O2 [M+H]+. found 443.44 at retention time 2.97 min.

後処理

  1. additionwas then introduced
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford 0.502 g of crude product, which
  8. customwas purified by chromatography (1% Methanol in DCM)

出典と根拠

ORDレコード
ord-9a56a8a3c3d847b3ac2ae6a59c17d9b4
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09428490B2

反応ノート

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