Tetrabutylammonium Fluoride → HCID 22733860, compound

HRID 2084603Notes

Reaction equation

HRID 2084603 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][Si](C(C)C)(C(C)C)C(C)C)[C:19]=3[O:35][CH3:36])=[O:17])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[C:19]=3[O:35][CH3:36])=[O:17])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 9936279HCID 9936279, compound

Product 1

HCID 22733860HCID 22733860, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Add to a solution of {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-methanone, Example 2C (1.80 g, 3.50 mmol) in dry THF (5 mL) at ca. 20° C. under nitrogen, 1.0 M tetrabutylammonium fluoride in THF (4.55 mL, 4.55 mmol). After stirring 5 h, dilute the reaction with brine (100 mL) and extract with CH2Cl2 (3×75 mL). Dry the extracts (Na2SO4) and concentrate under vacuum. Purify the crude product by column chromatography over silica gel eluting initially with 50:50 ethyl acetate/hexane then 5:95 methanol/ethyl acetate giving the product as an oil (Rf˜0.2 in ethyl acetate), which solidifies after standing. Triturate the solid with hexanes and recrystallize from hot ether (˜30 mL) by cooling and concentrating under a nitrogen stream to ˜10 mL. Collect the resulting slightly orange crystals to obtain 1.04 g (83%) of the title compound, mp 100-101° C.

Workup

  1. additiondilute
  2. extractionextract with CH2Cl2 (3×75 mL)
  3. dry with materialDry the extracts (Na2SO4)
  4. concentrationconcentrate under vacuum
  5. customPurify the crude product by column chromatography over silica gel eluting initially with 50:50 ethyl acetate/hexane
  6. customTriturate the solid with hexanes
  7. customrecrystallize from hot ether (˜30 mL)
  8. temperatureby cooling
  9. concentrationconcentrating under a nitrogen stream to ˜10 mL
  10. customCollect the resulting slightly orange crystals

Sources & evidence

ORD record
ord-42316789b4aa4479ae8cdc4e6db85db7
Source dataset
uspto-grants-2004_04
Patent number
US06716986B2

Reaction notes

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