Ammonium Chloride → 1-Tert-butoxycarbonyl-4-[2-(4-chloro-phenylsulfanyl)-5-trifluoromethyl-phenyl]-piperidine-4-ol

HRID 15229

Reaktionsgleichung

Reaktionsgleichung von HRID 15229
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[S:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Cl-].[NH4+]>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([OH:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 686834131-Bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 686846901-Tert-butoxycarbonyl-4-[2-(4-chloro-phenylsulfanyl)-5-trifluoromethyl-phenyl]-piperidine-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of n-butyl lithium (2.5 M in hexane, 6.5 mL, 16.2 mmol) was slowly added to a stirred solution of 1-bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzene (5.96 g, 16.2 mmol) in dry THF (40 mL) under argon at −78° C. The solution was stirred for 10 min before 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (3.23 g, 16.2 mmol) was added in one portion. The solution was allowed to warm to rt and then stirred overnight. Saturated aqueous ammonium chloride (80 mL) was added and the solution was extracted with ethyl acetate (80 mL). The organic phase was washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate and the solvent was evaporated off. The crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8) to produce the target compound as a white foam, yield: 4.53 g (57%).

Aufarbeitung

  1. additionwas added in one portion
  2. extractionthe solution was extracted with ethyl acetate (80 mL)
  3. washThe organic phase was washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated off
  6. customThe crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-e0a36d7253684b78aae29694191ea28d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732463B2

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