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

HRID 1728214
ノート
印刷プレビュー

反応式

HRID 1728214 の反応式
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3([CH3:27])[CH2:26][CH2:25]3)[C:5]2=[CH:4][CH:3]=1.[CH3:29][O:30][CH:31]([Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:32].[CH2:37](Br)[CH:38]=[CH2:39].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:39]([N:12]1[C:13](=[O:23])[CH2:14][CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:10]2([C:5]3[C:6](=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[NH:8][C:9]2=[O:28])[CH:11]1[C:24]1([CH3:27])[CH2:25][CH2:26]1)[CH:38]=[CH2:37].[CH3:29][O:30][CH:31]([Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:32]
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 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 77589972racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

生成物 1

HCID 77579449racemic (2'R,3R,4'S)-1'-allyl-6-bromo-4'-(3-chlorophenyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane
収率 97.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methyl cyclopropyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (200 mg, 0.34 mmol) and allyl bromide (1.2 g, 10 mmol) in DMF (15 mL) was added Cs2CO3 (4 g, 12.1 mmol). The mixture was stirred at room temperature for 2 h, then poured into water (100 mL), extracted with ethyl acetate for 3 times. The organic layer was washed with water, dried over Na2SO4, concentrated to give crude product as a light yellow solid (210 mg).

後処理

  1. extractionextracted with ethyl acetate for 3 times
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-b54de8706c224a99b8c2ccc83d22f208
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495007B2

反応ノート

読み込み中…

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