Methanol → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728207ノート

反応式

HRID 1728207 の反応式
[C:1]([CH:4]=[N:5][C:6]([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH2:7])([CH3:3])=[CH2:2].[Br:13][C:14]1[CH:22]=[C:21]2[C:17](/[C:18](=[CH:32]/[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)/[C:19](=[O:31])[N:20]2[CH2:23][O:24][CH2:25][CH2:26][Si](C)(C)C)=[CH:16][CH:15]=1.CO>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:22]=[C:21]2[NH:20][C:19](=[O:31])[C:18]3([CH:32]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[CH2:7][C:6](=[O:8])[NH:5][CH:4]3[C:1]([CH3:3])=[CH2:2])[C:17]2=[CH:16][CH:15]=1.[CH3:23][O:24][CH:25]([Si:9]([CH3:10])([CH3:11])[CH3:12])[CH3:26]

参加物

5

反応物 3

HCID 887MethanolHCID 765681151-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615101HCID 86615101、化合物

生成物 1

HCID 77581434racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane収率 33.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadiene (13 mmol) prepared in Example 87a in toluene was added E/Z-6-bromo-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one prepared in Example 161a (1.0 g, 2.16 mmol). The reaction mixture was refluxed under Argon for overnight. The mixture was cooled to room temperature, methanol (30 mL) was added, and then the mixture was concentrated. The residue was purified by chromatography (CH2Cl2:CH3OH=50:1) to give crude product (0.42 g).

後処理

  1. temperatureThe reaction mixture was refluxed under Argon for overnight
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified by chromatography (CH2Cl2:CH3OH=50:1)

出典と根拠

ORDレコード
ord-1c0a8d7585a04245affb4d97fb25d2c7
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

読み込み中…