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 1728207노트

반응식

HRID 1728207 반응식
[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]

참가 물질

5

반응물 3

HCID 887MethanolHCID 765681151-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615101HCID 86615101, 화합물

생성물 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 trimethylsilane수율 33.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1c0a8d7585a04245affb4d97fb25d2c7
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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