Sodium hydride → 4-(2-(4-Fluorophenylthio)eth-1-yl)-1-tert-butoxycarbonylpiperidine

HRID 2301182

Reaktionsgleichung

Reaktionsgleichung von HRID 2301182
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.I[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>O1CCCC1.CCOCC>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Produkt 1

HCID 181874814-(2-(4-Fluorophenylthio)eth-1-yl)-1-tert-butoxycarbonylpiperidineAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a slurry of sodium hydride (47 mg, 60% in mineral oil, 1.2 mmol) in tetrahydrofuran at 0° C. was added 4-fluorothiophenol (0.1 mL, 0.94 mmol). The reaction mixture was warmed to r.t. for 20 min, followed by addition of 4-(2-iodo-1-ethyl)-1-tert-butoxycarbonyl-piperidine (265 mg, 0.78 mmol, from Step C). The reaction was then heated to reflux for 10 min, cooled and diluted with ether. The organic layer was washed with 1 N NaOH, dried over MgSO4 and concentrated to provide 252 mg (95%) of the title compound. ESI-MS: 340.0 (M+H); HPLC A: 4.07 min.

Aufarbeitung

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 10 min
  3. temperaturecooled
  4. washThe organic layer was washed with 1 N NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db5a740d5315411b98cb0561110f776b
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498161B1

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