Water → (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one
Reaktionsgleichung
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C@H:25]1[CH2:44][N:28]2[C:29](=[O:43])[N:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=3)[CH2:31][C@@H:27]2[CH2:26]1)(C)(C)C.O>C1COCC1>[OH:24][C@H:25]1[CH2:44][N:28]2[C:29](=[O:43])[N:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:40])[F:41])=[CH:34][CH:33]=3)[CH2:31][C@@H:27]2[CH2:26]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Tetrabutyl ammonium fluoride (1.0 g, 3.8 mmol) was added to a solution of (6R,7aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (1.8 g, 3.3 mmol) in anhydrous THF (20 mL). The mixture was stirred for 2 hours at room temperature. The mixture was poured into water (50 mL), extracted with ethyl acetate (3×50 mL). The organic layers was combined, washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2=1:20) to give 0.95 g (94%) of the title compound.
Aufarbeitung
- extractionextracted with ethyl acetate (3×50 mL)
- washwashed with brine (50 mL)
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (MeOH/CH2Cl2=1:20)
Quellen und Nachweise
- ORD-Eintrag
- ord-9d7394586766416993563a9dcfbf164d
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08497288B2
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