Dimethylformamide → 2-(4-Chlorophenyl)-2-oxoethyl 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)-phenyl)piperidin-1-yl)methyl)butanoate

HRID 1051394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051394
[F:1][C:2]([F:26])([F:25])[CH:3]([CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10]1)[CH2:4][C:5]([OH:7])=[O:6].CCN(C(C)C)C(C)C.CN(C=O)C.Br[CH2:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)=[O:44]>C(OCC)(=O)C>[F:26][C:2]([F:1])([F:25])[CH:3]([CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)[CH2:10]1)[CH2:4][C:5]([O:7][CH2:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)=[O:44])=[O:6]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 68303p-Chlorophenacyl bromideHCID 81531DiisopropylethylamineHCID 901035704,4,4-Trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid

Produkt 1

HCID 901338472-(4-Chlorophenyl)-2-oxoethyl 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)-phenyl)piperidin-1-yl)methyl)butanoateAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 10 mL pear-shaped flask, 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid (50 mg, 130 μmol) and DIEA (50.6 mg, 68.3 μl, 391 μmol) were combined with DMF (2 ml) to give a colorless solution. 2-Bromo-1-(4-chlorophenyl)ethanone (60.9 mg, 261 μmol) was added and the resultant mixture was stirred at room temperature overnight. The reaction was diluted with ethyl acetate, washed with brine and H2O, dried with MgSO4, filtered and concentrated. The crude residue was purified on a silica column (100% hexane to 30% ethyl acetate/hexane eluent) to afford 54 mg (77%) of 2-(4-chlorophenyl)-2-oxoethyl 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)-phenyl)piperidin-1-yl)methyl)butanoate as an oil. MH+=536.

Aufarbeitung

  1. customto give a colorless solution
  2. washwashed with brine and H2O
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on a silica column (100% hexane to 30% ethyl acetate/hexane eluent)

Quellen und Nachweise

ORD-Eintrag
ord-3649333ec4b14c598eb858ec9caf8eb6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388172B2

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