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 1728207Notes

Reaction equation

HRID 1728207 reaction equation
[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]

Participants

5

Reactant 3

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

Product 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 trimethylsilaneYield 33.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1c0a8d7585a04245affb4d97fb25d2c7
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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