Fumaric Acid → (+/-)-2-Methyl-3-(3-pyridyl)-2-azabicyclo[2.2.2]octane Fumarate

HRID 581819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581819
[CH3:1][N:2]1[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]2[CH2:14][CH2:15][CH:3]1[CH2:4][CH2:5]2.[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20]>C(O)C>[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20].[CH3:1][N:2]1[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]2[CH2:14][CH2:15][CH:3]1[CH2:4][CH2:5]2

Komponenten

4

Edukt 2

HCID 444972Fumaric AcidHCID 18694214HCID 18694214, Verbindung

Produkt 1

HCID 23365584(+/-)-2-Methyl-3-(3-pyridyl)-2-azabicyclo[2.2.2]octane FumarateAusbeute 120,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of compound (XV) (120 mg, 0.495 mmol) in absolute ethanol (5 mL) was added fumaric acid (138 mg, 1.18 mmol). The resulting suspension was sonicated until complete dissolution occurred. The solvent was removed on a rotary evaporator to give a colorless syrup which was crystallized from absolute ethanol to yield 190 mg (88%) of compound (XVI). Mp=142°-143° C. 1H NMR(D2O+TSP): δ 8.71 (s, 1H), 8.64-8.62 (m, 1H), 8.30-8.22 (d, 1H), 7.79-7.72 (m, 1H), 6.60 (s, 3H), 4.58 (s, 1H), 3.90 (s, 1H), 2.90 (s, 3H), 2.80 (s, 1H), 2.46-2.38 (m, 1H), 2.10-1.95 (d, 2H), 1.92-1.62 (m, 5H).

Aufarbeitung

  1. customThe resulting suspension was sonicated until complete dissolution
  2. customThe solvent was removed on a rotary evaporator
  3. customto give a colorless syrup which
  4. customwas crystallized from absolute ethanol

Quellen und Nachweise

ORD-Eintrag
ord-09c19c27d4c74db1b901b42351a19f62
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922723

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