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(R)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide → (S)-N-((R)-(4-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide

HRID 1525273
Notes
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Reaction equation

HRID 1525273 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5](/[CH:6]=[N:7]/[S@@:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[CH:4][CH:3]=1.[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C@@H:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:7][S@:8]([C:10]([CH3:11])([CH3:12])[CH3:13])=[O:9])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12195522(R)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide2×HCID 178418255HCID 178418255, compound

Product 1

HCID 89462499(S)-N-((R)-(4-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamideYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

(R,E)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide, 18-b, (10 g, 34.84 mmol) was dissolved in anhydrous THF (100 ml). The mixture was then cooled to −45° C. and PhMgBr (34.84 ml, 69.68 mmol) was added dropwise. After addition, the mixture was allowed to stir at −45° C. for additional 4 h and warm to room temperature for another 2 h. TLC monitored the reaction and the time was prolonged if necessary. The mixture was quenched with saturated NH4Cl followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=4/1) to provide the product, 22-a, (8 g, 63%). HPLC indicated that the diastereomer ratio is 96:4 after recrystallization once in hexane/ethyl acetate.

Workup

  1. additionAfter addition
  2. temperaturewarm to room temperature for another 2 h
  3. customthe reaction
  4. customThe mixture was quenched with saturated NH4Cl
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8cdf44e600db40d29722f3475d55fddc
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079930B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes