tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

HRID 522855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522855
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 18364827tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 11301928Tert-butyl 4-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(4-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (2.5 g, 0.00783 mol) (prepared as described in Reference G above) in ethanol (23.0 mL) was added 10% Pd/C (826 mg, 0.00078 mol) under N2 atmosphere and the mixture was allowed to stir at RT overnight under hydrogen atmosphere. The reaction mixture was filtered through cellite, washing with EtOAc (2×100 mL). The filtrate was concentrated under reduced pressure to obtain 4-(4-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (2 g, 80%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through cellite
  2. washwashing with EtOAc (2×100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-033d881bab674d9cb293bd215b1fc8ec
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334269B2

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