Ammonium Chloride → tert-butyl (3S,4S)-4-(4-amino-2-chlorophenoxy)-3-fluoropiperidine-1-carboxylate
Reaktionsgleichung
[Cl:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@@H:6]1[F:18].[NH4+].[Cl-]>CCO.O.CCOC(C)=O.[Fe]>[NH2:23][C:21]1[CH:20]=[CH:19][C:3]([O:4][C@H:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][C@@H:6]2[F:18])=[C:2]([Cl:1])[CH:22]=1Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
A mixture of tert-butyl (3S,4S)-4-(2-chloro-4-nitrophenoxy)-3-fluoropiperidine-1-carboxylate (0.8 g, 1.0 eq, 2.2 mmol), Fe (0.6 g, 5.0 eq, 10.8 mmol) and NH4Cl (0.6 g, 5.0 eq, 10.8 mmol) in EtOH/H2O (1:1, 50 mL) was stirred at 90° C. for 1 hour. The mixture was cooled to room temperature and concentrated under reduced pressure to leave a crude solid. The crude mixture was dissolved in EtOAc (50 mL) and partitioned with H2O (50 mL). Organic layers were separated and the aqueous layer was washed with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give the desired product in 45% yield. This product was taken to next step with out further purification.
Aufarbeitung
- temperatureThe mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- customto leave a crude solid
- custompartitioned with H2O (50 mL)
- customOrganic layers were separated
- washthe aqueous layer was washed with EtOAc (50 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-1902c28a453d4b70bd690f74c441e576
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321763B2
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