Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate → Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate

HRID 515316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515316
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 18538797Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate

Produkt 1

HCID 18538812Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylateAusbeute 108,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(4-nitrophenylthio)piperidine-1-carboxylate (8.56 mmol, 2.8973 g) and palladium (3.77 mmol, 0.401 g) were combined in ethanol (30 mL) and the reaction mixture hydrogenated at 5 bar for 2 hours. The reaction mixture was filtered and concentrated under vacuum, reaction incomplete. Hydrogenation resumed with fresh palladium and left overnight. The reaction mixture was filtered and concentrated under vacuum to afford the title compound (2.86 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum, reaction incomplete
  3. waitleft overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-01639aa61da4456a8295f845ae20d100
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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