Tetrabutylammonium Fluoride → Tetrabutylammonium Fluoride

HRID 1047375Notes

Reaction equation

HRID 1047375 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(C)(C)C.[F-:27].[CH2:28]([N+:32]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>O1CCCC1.C(OCC)C>[F:22][C:21]([S:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([OH:6])[CH2:8][CH2:9]2)=[CH:19][CH:18]=1)([F:24])[F:23].[F-:27].[CH2:41]([N+:32]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455360HCID 178455360, compound

Product 2

HCID 2724141Tetrabutylammonium FluorideHCID 178521585HCID 178521585, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

[Trans-4-(tert-butyl-dimethyl-silyloxy)-cyclohexyl]-(4-trifluoromethylsulfanyl-phenyl)-amine (180 mg, 0.44 mmol, prepared in accordance with Example 28) was dissolved in tetrahydrofuran (3 mL). A molar solution of tetrabutylammonium fluoride (500 μL, 5 mmol) was then added. The resulting mixture was heated to 40° C. and then maintained at that temperature for 4 hr. After cooling to room temperature, the mixture was diluted with diethylether (20 mL), washed with water (10 mL), and washed with saturated aqueous hydrogencarbonate (10 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The oily residue obtained was purified by column chromatography on silica gel (dichloromethane and then dichloromethane/methanol, 95:5). The desired product was isolated as a colorless oil with traces of tetrabutylammonium fluoride.

Workup

  1. temperaturemaintained at that temperature for 4 hr
  2. temperatureAfter cooling to room temperature
  3. washwashed with water (10 mL)
  4. washwashed with saturated aqueous hydrogencarbonate (10 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe oily residue obtained
  10. customwas purified by column chromatography on silica gel (dichloromethane

Sources & evidence

ORD record
ord-0640e61b4f324e0c9dd65ac67ef6549f
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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