(NE,R)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide → (R)-N-((R)-(3-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide

HRID 1525281Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)/[CH:5]=[N:6]/[S@@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8].[Li][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:6][S@@:7]([C:9]([CH3:11])([CH3:12])[CH3:10])=[O:8])[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(R,E)-N-(3-bromobenzylidene)-2-methylpropane-2-sulfinamide, 24-b, (12 g, 41.64 mmol) was dissolved in anhydrous THF (120 ml). The mixture was then cooled to −78° C. and PhLi (41 ml, 83.28 mmol) was added dropwise. After addition the mixture was allowed to stir at −78° C. for additional 2 h and warmed to room temperature for another 2 h. 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=5/1) to provide the product, 24-c, (11.8 g, 77%). HPLC indicated that the diastereomer ratio is 90:10 and the product was used for the next step directly.

Workup

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

Sources & evidence

ORD record: ord-65e80758b45543f4ac69b14abb8b8dcf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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