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Diiodomethane → 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

HRID 1728211
Notes
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Reaction equation

HRID 1728211 reaction equation
ICI.[CH2:4]([Zn]CC)C.[Br:9][C:10]1[CH:15]=[C:14]2[NH:16][C:17](=[O:35])[C:18]3([CH:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=4)[CH2:22][C:21](=[O:31])[NH:20][CH:19]3[C:32]([CH3:34])=[CH2:33])[C:13]2=[CH:12][CH:11]=1.[CH3:36][O:37][CH:38]([Si:40]([CH3:43])([CH3:42])[CH3:41])[CH3:39]>C1(C)C=CC=CC=1>[Br:9][C:10]1[CH:15]=[C:14]2[NH:16][C:17](=[O:35])[C:18]3([CH:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=4)[CH2:22][C:21](=[O:31])[NH:20][CH:19]3[C:32]3([CH3:4])[CH2:34][CH2:33]3)[C:13]2=[CH:12][CH:11]=1.[CH3:36][O:37][CH:38]([Si:40]([CH3:43])([CH3:42])[CH3:41])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 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 trimethylsilaneHCID 178418750HCID 178418750, compound

Product 1

HCID 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 trimethylsilaneYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diiodomethane (3.7 g, 0.013 mmol) in toluene (10 mL) was cooled in ice-salt bath. Then diethylzinc (1.1M in toluene, 10 mL, 11 mmol) was added dropwise into the above solution slowly. After the addition, the mixture was stirred for 10 min. To the resulting mixture was added a solution 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 prepared in Example 267a (800 mg, 1.4 mmol) in toluene (10 mL). The mixture was then allowed to warm to room temperature and stirred for 3 h, quenched with aqueous NH4Cl. The organic layer was separated, washed with water, dried over Na2SO4, purified by column chromatography to give title compound (800 mg).

Workup

  1. additionAfter the addition
  2. stirringstirred for 3 h
  3. customquenched with aqueous NH4Cl
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-4a57aabfdab1430b8a46711ab985014f
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495007B2

Reaction notes

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