1-Acetoxy-2-bromoethane → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2-hydroxyethyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728208Notes

Reaction equation

HRID 1728208 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].BrCCOC(=O)C.[H-].[Li+]>C(OCC)(=O)C>[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])[N:12]([CH2:31][CH2:30][OH:29])[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]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 62714Lithium hydrideHCID 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 77579633racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2-hydroxyethyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 70.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 (150 mg, 0.26 mmol) and acetic acid 2-bromo-ethyl ester (867 mg, 5.22 mmol) was added LiH (63 mg, 7.9 mmol). The mixture was stirred at room temperature for 20 h, then diluted with ethyl acetate (10 mL), quenched with water (10 mL). The organic layer was separated, washed with water for 5 times, dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give product (57 mg).

Workup

  1. customquenched with water (10 mL)
  2. customThe organic layer was separated
  3. washwashed with water for 5 times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-30aa566382724fba854686ac26ee8a2f
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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