Potassium Carbonate → Tert-butyl 4-(2-chlorophenylthio)piperidine-1-carboxylate

HRID 2356223

Reaktionsgleichung

Reaktionsgleichung von HRID 2356223
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[SH:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cl-].[Na+].O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Produkt 1

HCID 58724129Tert-butyl 4-(2-chlorophenylthio)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.00 g, 7.16 mmol, prepared according to Blurton et al., WO 00/43362), 2-chlorobenzenethiol (0.898 ml, 7.88 mmol), and potassium carbonate (1.58 g, 11.5 mmol) were stirred together in acetonitrile (15 ml). The reaction was heated to 75° C. and was stirred at that temperature for 15 h. After cooling to room temperature, brine was added, and the mixture was extracted with EtOAc three times. Combined organic layers were dried over MgSO4, filtered and concentrated in vacuo.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc three times
  3. dry with materialCombined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2cc7da808700437b9b7daf0a7c8d0497
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759339B2

Verknüpfte Notizen

Wird geladen…