Tetrabutylammonium Fluoride → 1638667-81-8

HRID 1854578Notes

Reaction equation

HRID 1854578 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:20]([OH:23])([CH3:22])[CH3:21])[C@H:12]([CH3:24])[N:11]1[C:25](=[O:35])[CH2:26][C:27]1[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:34])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[CH2:26][C:25]([N:11]1[C@@H:10]([CH2:9][OH:8])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:20]([OH:23])([CH3:21])[CH3:22])[C@@H:12]1[CH3:24])=[O:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123347188HCID 123347188, compound

Product 1

HCID 1177202721638667-81-8Yield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxypropan-2-yl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (0.054 g, 100 μmol) in THF (1.0 mL). Add tetrabutylammonium fluoride (0.11 mL, 110 μmol, 1M in THF). Stir 30 min. Add saturated ammonium chloride solution and extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 10-100%) to give the title compound as a white foam (0.03 g, 71 μmol). MS (m/z): 422 (M+1).

Workup

  1. extractionAdd saturated ammonium chloride solution and extract with ethyl acetate three times
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customto give a residue
  6. customPurify the residue by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-fcf58f3d9da743fe932ddbecccb4f39e
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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