(Trifluoromethyl)trimethylsilane → 1-(Diphenylmethyl)-3-(trifluoromethyl)azetidin-3-ol
Reaktionsgleichung
[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH:1]([N:14]1[CH2:17][C:16]([C:20]([F:22])([F:21])[F:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
1-Benzhydrylazetidin-3-one (5.0 g, 1.0 eq.) was dissolved in THF (50 mL). Trifluoromethyl trimethylsilane was added at 5-10° C. The reaction mixture was stirred at 10° C. for 10 min. Tetrabutyl ammonium fluoride was then added. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by chromatography (6% ethyl acetate-hexane) to give 3 g of 1-benzhydryl-3-(trifluoromethyl)azetidin-3-ol (Yield: 46.32%).
Aufarbeitung
- temperatureto warm to room temperature
- stirringstirred for 1 h
- washwashed with water and brine
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customto give the crude product, which
- customwas purified by chromatography (6% ethyl acetate-hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-4c39dfb18ced420d9a41a26f4c650f41
- Quelldatensatz
- uspto-grants-2016_08
- Patentnummer
- US09428490B2
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