Tetrahydrofuran → HCID 22643288, Verbindung

HRID 2414846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414846
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:26][O:25][C:16]3[CH:17]=[CH:18][C:19]4[N:20]=[C:21]([CH3:24])[O:22][C:23]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.FC(F)(F)[C:29]1[CH:30]=[C:31]([C:35]2[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=2)[CH:32]=[CH:33][CH:34]=1.C1COCC1.C(O)(=O)/C=C/C(O)=O>CN(C=O)C.C(O)C>[CH3:24][C:21]1[O:22][C:23]2=[C:15]3[C:16](=[CH:17][CH:18]=[C:19]2[N:20]=1)[O:25][CH2:26][CH:13]([CH2:12][N:38]1[CH2:37][CH:36]=[C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:29][CH:30]=2)[CH2:40][CH2:39]1)[O:14]3

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 444972Fumaric AcidHCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineHCID 11245807(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate

Produkt 1

HCID 22643288HCID 22643288, VerbindungAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate (0.40 g, 1.1 mmole) and 4-(3-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyridine (0.35 g, 1.54 mmole) were combined in 5 mL of DMF and 5 ml of THF under nitrogen. This solution was refluxed under nitrogen for overnight. After completion, the reaction was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The resulting crude oil was column chromatographed on silica gel using first methylene chloride to remove impurities and then 1% methanol/methylene chloride to elute the (S)-enantiomer of the title compound. This was recrystallized from ethanol with the addition of one equivalent of fumaric acid to give 80 mg of white solid, m.p. 170-173° C.

Aufarbeitung

  1. temperatureThis solution was refluxed under nitrogen for overnight
  2. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using first methylene chloride
  7. customto remove impurities
  8. wash1% methanol/methylene chloride to elute the (S)-enantiomer of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-8fecabd3a8fa4e1c8d246b92ebec0793
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815448B2

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