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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
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HRID 1728214 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 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
수율 97.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b54de8706c224a99b8c2ccc83d22f208
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495007B2

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