Reaktionsgleichung
[C:1]([C@H:3]1[CH2:7][N:6](C(OC(C)(C)C)=O)[C@H:5]([C:15](=[O:31])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[CH2:4]1)#[N:2]>Cl>[C:1]([C@H:3]1[CH2:7][NH:6][C@H:5]([C:15]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[CH:21][CH:22]=2)=[O:31])[CH2:4]1)#[N:2]Komponenten
3
Versuchsvorschrift
The crude (2S,4R)-tert-butyl 4-cyano-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate was combined with hydrogen chloride (4N in dioxane, 20 mL). The mixture was stirred at ambient temperature for 1 hour and then quenched with saturated sodium bicarbonate (aq., 100 mL). The mixture was extracted with ethyl acetate (30 mL) and the extract was washed with deionized water (30 mL) and then brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was triturated with ethyl acetate to give (2S,4R)-4-cyano-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (0.88 g, 2.69 mmol, 65% yield over 2 steps) as an off-white solid.
Aufarbeitung
- customquenched with saturated sodium bicarbonate (aq., 100 mL)
- extractionThe mixture was extracted with ethyl acetate (30 mL)
- washthe extract was washed with deionized water (30 mL)
- dry with materialbrine (30 mL), dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was triturated with ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-1d8ac74da33947c78a6756ca09ab2d45
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08791102B2
Verknüpfte Notizen
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