Water → 2-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-2-(trifluoromethyl)oxirane

HRID 600748

Reaktionsgleichung

Reaktionsgleichung von HRID 600748
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([C:11]1([CH2:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH3:10].O>CS(C)=O.C1COCC1>[CH2:9]([C:11]1([CH2:21][C:22]2([C:23]([F:24])([F:26])[F:25])[CH2:4][O:27]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH3:10]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11694680HCID 11694680, Verbindung2×

Produkt 1

HCID 116305852-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-2-(trifluoromethyl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (74 mg of a 60% dispersion in mineral oil, 1.85 mmol) in DMSO (5 ml) was added a solution of trimethylsulphoxonium iodide (610 mg, 2.77 mmol) in DMSO (5 ml). After stirring at room temperature for 30 min a solution of 3-(1-ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)-1,1,1-trifluoro-2-propanone (Intermediate 13) (500 mg, 1.85 mmol) in THF (3 ml) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water and extracted with diethylether. The organic extract was washed repeatedly with water, dried over anhydrous sodium sulphate and evaporated in vacuo to give the title compound as a crude mixture of diastereomers. Extraction of aqueous layer with dichloromethane yielded further title compound as a crude mixture of diastereomers. Combined products were then applied to a 20 g silica SPE cartridge eluting with a 0-10% dichloromethane in cyclohexane gradient for 10 min followed by 10% dichloromethane in cyclohexane for 5 min. This gave, in order of elution, Intermediate 14 (racemic diastereomer 1, 178 mg): and Intermediate 15 (racemic diastereomer 2, 86 mg).

Aufarbeitung

  1. additionwas added
  2. extractionextracted with diethylether
  3. extractionThe organic extract
  4. washwas washed repeatedly with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-83c66d913b62428db201f738f3a3287a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902224B2

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