Tetrabutylammonium Fluoride → HCID 178464454, Verbindung

HRID 2057295

Reaktionsgleichung

Reaktionsgleichung von HRID 2057295
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:37][CH3:38])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N+:21]([O-:36])([CH3:35])[S:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:17][CH2:16]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:37]([N:9]([CH2:8][CH2:7][OH:6])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N+:21]([O-:36])([CH3:35])[S:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=2)(=[O:23])=[O:24])[CH2:17][CH2:16]1)[CH3:38]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 178463969HCID 178463969, Verbindung

Produkt 1

HCID 178464454HCID 178464454, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 335 mg (5.5 mmol) trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide in 8 ml THF were added 0.83 ml 1M TBAF at 0° C. The solution was stirred at RT for 1 h, partitioned between EtOAc and an aqueous solution of Na2CO3. The organic phase was washed with brine and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 9:1 yielded 190 mg (44%, 3 steps) trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide N-oxide as colorless oil, MS: 495 (MH+).

Aufarbeitung

  1. custompartitioned between EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-3bc60bece80d4de994b3bb15ce6531d6
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

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