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Acetic Acid → rac-(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile

HRID 909014
ノート
印刷プレビュー

反応式

HRID 909014 の反応式
[Cl:1][C:2]1[C:3]([F:20])=[C:4](/[CH:8]=[C:9](/[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[F:19])\[C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.[CH3:21][C:22]([CH3:32])([CH3:31])[CH2:23]/[CH:24]=[N:25]/[CH2:26][Si](C)(C)C.C(O)(=O)C.O>CN(C)P(N(C)C)(N(C)C)=O>[Cl:1][C:2]1[C:3]([F:20])=[C:4]([CH:8]2[CH2:26][NH:25][CH:24]([CH2:23][C:22]([CH3:32])([CH3:31])[CH3:21])[C:9]2([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[F:19])[C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1
参加物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 176Acetic AcidHCID 962Water2 回HCID 58222849(E)-3,3-dimethyl-N-(trimethylsilylmethyl)butan-1-imineHCID 59249629(Z)-3-(3-Chloro-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile

生成物 1

HCID 67095302rac-(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile収率 24.4%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile (1.2 g, 3.87 mmol) in hexamethylphosphoramide (20 mL) was added [3,3-dimethyl-but-(E)-ylidene]-trimethylsilanylmethyl-amine (1.1 g, 5.9 mmol), acetic acid (60 mg, 1 mmol) and H2O (0.1 g, 5.6 mmol) sequentially. The reaction mixture was stirred at room temperature for 18 h. Water was added. The mixture was extracted with ethyl acetate. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water twice, dried over MgSO4, then concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4, 1;3) to give rac-(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile as a white foam (0.4 g, 24%).

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate
  4. washwashed with water twice
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1:4, 1;3)

出典と根拠

ORDレコード
ord-513cc70eb8514c9f8b113bad69f8c7a6
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017607B2

反応ノート

読み込み中…

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