Ethyl Acetate → racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728209Notes

Reaction equation

HRID 1728209 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:27])[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]([CH3:26])=[CH2:25])[C:5]2=[CH:4][CH:3]=1.[CH3:28][O:29][CH:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH3:31].Br[CH2:37][C:38]([NH2:40])=[O:39].C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[NH2:40][C:38]([CH2:37][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:27])[CH:11]1[C:24]([CH3:26])=[CH2:25])=[O:39].[CH3:28][O:29][CH:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH3:31]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonate2×HCID 696322-Bromoacetamide2×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

Product 1

HCID 77580112racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 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 (100 mg, 0.17 mmol) and 2-bromo-acetamide (72 mg, 0.52 mmol) in DMF (1 mL) was added Cs2CO3 (332 mg, 1.01 mmol). The mixture was stirred at room temperature for overnight. Then additional 2-bromo-acetamide (72 mg, 0.52 mmol) and Cs2CO3 (332 mg, 1.01 mmol) were added to the reaction mixture. The resulting mixture was heated at 50° C. for 2 h, then poured into ethyl acetate (20 mL). The organic layer was washed with water 3 times, dried over Na2SO4, purified by column chromatography to give title compound 60 mg.

Workup

  1. temperatureThe resulting mixture was heated at 50° C. for 2 h
  2. washThe organic layer was washed with water 3 times
  3. dry with materialdried over Na2SO4
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-0d6a6391893243d0958191ebbc0f0998
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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