Triethylamine → (R)-3-(8-(4-fluoro-3-methylphenyl)octanoyl)-4-isopropyloxazolidin-2-one

HRID 885521

Reaktionsgleichung

Reaktionsgleichung von HRID 885521
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][C:3]=1[CH3:18].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[Li+].[Cl-].[CH:35]([C@@H:38]1[CH2:42][O:41][C:40](=[O:43])[NH:39]1)([CH3:37])[CH3:36]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:39]2[C@H:38]([CH:35]([CH3:37])[CH3:36])[CH2:42][O:41][C:40]2=[O:43])=[O:17])=[CH:4][C:3]=1[CH3:18]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-oneHCID 595125948-(4-Fluoro-3-methylphenyl)octanoic acid

Produkt 1

HCID 69169742(R)-3-(8-(4-fluoro-3-methylphenyl)octanoyl)-4-isopropyloxazolidin-2-oneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a cooled (−10° C.) solution of 8-(4-fluoro-3-methylphenyl)octanoic acid (0.486 g, 1.926 mmol) in 15 mL of THF, were added stepwise triethylamine (0.69 mL, 4.952 mmol) and pivaloyl chloride (0.23 mL, 1.889 mmol). The reaction mixture was stirred at −10° C. for 1 h and then LiCl (0.080 g, 1.889 mmol) and (R)-4-iso-propyloxazolidin-2-one (0.237 g, 1.834 mmol) were added stepwise. After being warmed slowly to room temperature and stirred for overnight, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.547 g, 82% yield). GC-MS: tR=6.9 min; m/z 363 (M+).

Aufarbeitung

  1. temperatureAfter being warmed slowly to room temperature
  2. stirringstirred for overnight
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was isolated by Flash column chromatography (silica gel column)
  8. washeluting with 0-100% dichloromethane/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-18909bd925054872a72a8be1172e91ad
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242174B2

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