Tetrabutylammonium Fluoride → HCID 25253850, compound

HRID 1629672Notes

Reaction equation

HRID 1629672 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:17][CH:16]=2)[CH2:6][CH:5]1[CH3:40])(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=2)[CH2:6][CH:5]1[CH3:40])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66625010HCID 66625010, compound

Product 1

HCID 25253850HCID 25253850, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[Step 3] 615 mg of 1-acetyl-4-[(4-tert-butyldiphenylsilyloxymethylphenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 2 mL of tetrahydrofuran, and 2.8 mL of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) was added to the solution. The mixture was stirred for 3 hours at room temperature. After completion of the reaction, the reaction liquid was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (developing solvent: ether only), and thus 264 mg (79%) of 1-acetyl-4-[(4-hydroxymethylphenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a yellow oily substance (cis:trans=3:1).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-f393453158af4765b0634a22b495f970
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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