Tetrabutylammonium Fluoride → N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide

HRID 1785983Notes

Reaction equation

HRID 1785983 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:34]=[CH:35][C:36]=1[F:37])[C:10]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:15]([N:22]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:23](=[O:25])[CH3:24])[CH2:14][C@@H:13]1[CH3:33])=[O:11])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>ClCCl>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([N:22]([C@H:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([C:10](=[O:11])[C:9]3[CH:34]=[CH:35][C:36]([F:37])=[C:7]([OH:6])[CH:8]=3)[C@@H:13]([CH3:33])[CH2:14]2)[C:23](=[O:25])[CH3:24])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68920733N-[(2S,4R)-1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-fluorobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-(4-chlorophenyl)acetamide

Product 1

HCID 57595472N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamideYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(2S,4R)-1-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-fluorobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-(4-chlorophenyl)acetamide (543 mg, 0.95 mmol) was dissolved in dichloromethane and a solution of TBAF (1.0 M in THF, 5.0 mL) was added; the reaction mixture was stirred at room temperature for until no starting material remained. The reaction was washed with sat. NaHCO3 and brine carefully. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography using Hexanes-EtOAc system to give N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (477 mg, 100%).

Workup

  1. washThe reaction was washed with sat. NaHCO3 and brine carefully
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5c62ccf86eb749f88ae578bd3cd8560d
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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