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Benzene, 1-iodo-4-(trifluoromethyl)- → 4-[2-(4-Trifluoromethyl-phenylsulfanyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 15238
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 15238
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1.CC(C)([O-])C.[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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Komponenten

7

Edukt 4

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 686357834-(2-Triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 686811394-[2-(4-Trifluoromethyl-phenylsulfanyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester
Ausbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 4-(2-tri-iso-propylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (38 mg, 0.085 mmol) and 1-iodo-4-trifluoromethyl-benzene (23 mg, 0.085 mmol) was dissolved in dry degassed toluene (0.3 mL). Pd2dba3 (1 mg) and DPEphos (1 mg) dissolved in dry toluene (0.2 mL) were added. To this solution were added potassium tert-butoxide (10 mg) and tetra-n-butyl ammonium fluoride (TBAF, 1M in TBF, 0.1 mL, 0.1 mmol) and the reaction mixture was stirred at 110° C. for 1 h under argon. The solution was filtered and the solvent was evaporated off. The crude product was purified by chromatography on silica gel (eluent: An increasing amount (0-100%) of ethyl acetate in heptane) to produce 4-[2-(4-trifluoromethyl-phenylsulfanyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (3a1) as a clear oil (22 mg, 59% yield). This material was dissolved in methanol (1 mL) and hydrogen chloride in diethyl ether (2M, 1 mL) was added and the solution was stirred overnight at rt. The solvent was evaporated of and the crude product was purified by BPLC (containing 0.1% TFA in the standard eluent) to produce 4-[2-(4-trifluoromethyl-phenylsulfanyl)-phenyl]-piperidine 3a1 as the trifluoro-acetic acid salt. Yield: 3.2 mg (8% overall). LC/TOF (m/z) 338.0 (MH+); RT=2.29 min; purity (UV, ELSD): 98.3%, 97.1%.

Aufarbeitung

  1. dissolutionwas dissolved
  2. customin dry
  3. customdegassed toluene (0.3 mL)
  4. dissolutionPd2dba3 (1 mg) and DPEphos (1 mg) dissolved in dry toluene (0.2 mL)
  5. additionwere added
  6. filtrationThe solution was filtered
  7. customthe solvent was evaporated off
  8. customThe crude product was purified by chromatography on silica gel (eluent

Quellen und Nachweise

ORD-Eintrag
ord-e00a7c67eda048cfa266d1f33c8a8c27
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07732463B2

Notizen zur Reaktion

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