Methanol → cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-1-ethyl-3-phenylpiperidine oxalate

HRID 1437677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437677
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([O:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=2)[C@H:6]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:5]1)(=O)[CH3:2].CO.[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]>C1COCC1.B>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[F:25][C:22]([F:23])([F:24])[C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=1)[CH2:11][O:10][C@H:7]1[CH2:8][CH2:9][N:4]([CH2:1][CH3:2])[CH2:5][C@H:6]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 971Oxalic AcidHCID 86606806HCID 86606806, Verbindung

Produkt 1

HCID 86606828cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-1-ethyl-3-phenylpiperidine oxalateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6331BoraneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of the compound (0.88 g) obtained in Example 2 in THF (10 ml), 1 M borane and THF complex (10 ml) was added at 0° C., and the reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled, and then methanol (2 ml) was added thereto, and concentrated under reduced pressure. To the obtained residue, 6 N hydrogen chloride (6 ml) and methanol (6 ml) were added, and the reaction mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled, and then made basic with an aqueous 12 N sodium hydroxide solution. The mixture was concentrated under reduced pressure, and then the product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (acetone:methanol=20:1), and treated with 1 equivalent of oxalic acid to obtain the title compound as colorless crystals (0.52 g, 61%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionTo the obtained residue, 6 N hydrogen chloride (6 ml) and methanol (6 ml) were added
  4. stirringthe reaction mixture was stirred at 100° C. for 2 hours
  5. temperatureThe reaction mixture was cooled
  6. concentrationThe mixture was concentrated under reduced pressure
  7. extractionthe product was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. customdried
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was isolated
  12. custompurified by silica gel column chromatography (acetone:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-19caceb67bd04323be69a9591db73262
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622487B2

Notizen zur Reaktion

Wird geladen…