Ammonium formate → tert-Butyl cis(+/-)-4-amino-3-(benzyloxy)piperidine-1-carboxylate
Reaktionsgleichung
C([O-])=O.[NH4+].C([NH:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
10% Pd/C (wet, 1.1 g) and ammonium formate (2.87 g, 46 mmol) were added to a solution of tert-butyl cis(±)-4-(benzylamino)-3-(benzyloxy)piperidine-1-carboxylate obtained in Example (90c) (4.84 g, 11.4 mmol) in methanol (30 mL) in a nitrogen atmosphere, and the mixture was stirred at 70° C. for 40 minutes. The reaction solution was filtered to remove the Pd/C. Following concentration under reduced pressure, a 1 N aqueous sodium hydroxide solution was added to the residue, followed by extraction with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, to obtain 3.15 g of the crude title compound as a colorless oily substance (94%).
Aufarbeitung
- filtrationThe reaction solution was filtered
- customto remove the Pd/C
- concentrationconcentration under reduced pressure
- additiona 1 N aqueous sodium hydroxide solution was added to the residue
- extractionfollowed by extraction with dichloromethane three times
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-09f26b3182e34b3584bfbf2f2c7d972b
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536197B2
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