Acetic Acid → Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

HRID 1250695

Reaktionsgleichung

Reaktionsgleichung von HRID 1250695
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 176Acetic Acid2×HCID 18326592tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-[1-tert-butoxycarbonyl-(1,2,3,6-tetrahydropyrdin-4-yl)]benzonitrile (5.3 g, 0.019 mol) and acetic acid (0.28 ml, 4.9 mmol) in ethanol (200 ml), degassed with argon was added palladium on carbon. The reaction was hydrogenated on a Parr capparatus at 50 psi for 15 hours. The mixture was recharged twice with acetic acid (0.14 ml, 0.28 ml) and palladium on carbon (900 mg, 1.8 g), hydrogenated as above and filtered through celite. Solvent evaporation gave 2-(1-tert-butoxycarbonylpiperidin-4-yl)benzonitrile; 1H NMR (CDCl3) d 1.49 (s, 9H), 1.64 (m, 2H), 1.86 (bd, 2H, J=13.4 Hz), 2.88 (bt, 2H, J=14 Hz), 3.14 (tt, 1H, J=12 Hz, J=4 Hz), 4.27 (bs, 2H), 7.31 (m, 2H), 7.56 (bt, 1H, J=7.7 Hz), 7.63 (bd, 1H, J=7.7 Hz).

Aufarbeitung

  1. filtrationhydrogenated as above and filtered through celite
  2. customSolvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-39941b7a8fd549bda75238eeba5982b6
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339090B1

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