Trifluoroacetic acid → methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

HRID 1810790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810790
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:13](CC3C=CC(OC)=CC=3)[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=2[CH:27]=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=2[CH:27]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68650162methyl 9-bromo-1-(4-methoxybenzyl)-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

Produkt 1

HCID 68649852methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylateAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 9-bromo-1-(4-methoxybenzyl)-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (12.5 g) in toluene (62.5 ml) was added trifluoroacetic acid (62.5 ml) and the mixture was stirred under nitrogen atmosphere at 80° C. for 7 hours. After distilling off the solvent under reduced pressure, water was added at 0° C. and the mixture was neutralized with potassium carbonate, and extracted with ethyl acetate. After washing the organic layer with aqueous saturated sodium bicarbonate solution and saturated brine, the resultant was dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=9:1) and recrystallized from hexane:ethyl acetate to give methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (7.4 g) as yellow crystals.

Aufarbeitung

  1. distillationAfter distilling off the solvent under reduced pressure, water
  2. additionwas added at 0° C.
  3. extractionextracted with ethyl acetate
  4. washAfter washing the organic layer with aqueous saturated sodium bicarbonate solution and saturated brine
  5. dry with materialthe resultant was dried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=9:1)
  8. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-d81eb484a3324e65a13e085ab659d9bf
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362058B2

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