Reaktionsgleichung
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)(=O)[NH2:2].O=P(Cl)(Cl)Cl.CC(=O)OCC>N1C=CC=CC=1>[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)#[N:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A 250-mL 3-necked round-bottomed flask was charged with a solution of tert-butyl 3-carbamoylpiperidine-1-carboxylate (5 g, 21.49 mmol, 1.00 equiv, 98%) in pyridine (50 mL). To this solution, POCl3 (5 g, 32.24 mmol, 1.50 equiv, 98%) was added drop wise at 0° C. and allowed to stir at 0° C. for 1 hour. The progress was monitored by TLC (EA:PE=1:1). The pyridine was removed by distillation. The mixture was diluted with H2O (40 mL) and pH was adjusted to 8 by addition of aqueous NaHCO3. Then, the resulting mixture was extracted with ethyl acetate (3×30 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The crude was purified by distillation under reduced pressure (30 mm Hg) and the fractions collected at 40° C. to afford tert-butyl 3-cyanopiperidine-1-carboxylate as yellow oil (2.6 g, 53%).
Aufarbeitung
- customThe pyridine was removed by distillation
- additionThe mixture was diluted with H2O (40 mL) and pH
- additionwas adjusted to 8 by addition of aqueous NaHCO3
- extractionThen, the resulting mixture was extracted with ethyl acetate (3×30 mL)
- dry with materialCombined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered off
- concentrationconcentrated on a rotary evaporator
- distillationThe crude was purified by distillation under reduced pressure (30 mm Hg)
- customthe fractions collected at 40° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-e29aefe7c1384759844d188b93d1353a
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08080566B1
Verknüpfte Notizen
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