Ammonium formate → Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

HRID 238268

Reaktionsgleichung

Reaktionsgleichung von HRID 238268
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 18326592tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4-(2-Cyano-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.2 g) was dissolved in IMS (15 mL) and palladium on carbon (10%; 0.08 g) in water (0.5 mL) was added. Ammonium formate (0.3 g) was added and the mixture heated at reflux for 0.5 hour. The mixture was allowed to cool, filtered and the solvent removed by evaporation to give the title compound as a clear colourless oil (0.15 g). LCMS m/z 287.3[M+H]+. R.T.=4.63 min (Analytical Method 4).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 0.5 hour
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-6c6b8b24a291417584e13c73563824ae
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642621B2

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