Acetic Acid → HCID 86659845, Verbindung

HRID 2402740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402740
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][C@@H:16]2[C:18](=[CH2:21])[CH2:19][CH2:20][C@@H:15]2[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=[O:24])C.[C:26](#[N:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:6]([N:13]1[CH2:17][C@@H:16]2[C@:18]([NH:33][C:26](=[O:24])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([CH3:21])[CH2:19][CH2:20][C@@H:15]2[CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 11629873HCID 11629873, Verbindung

Produkt 1

HCID 86659845HCID 86659845, Verbindung

Versuchsvorschrift

Sulfuric acid (1.437 mL, 27.0 mmol) was added to a solution of (3aS,6aS)-2-benzyl-4-methyleneoctahydrocyclopenta[c]pyrrole (0.575 g, 2.70 mmol, Example 1) in acetic acid (1.466 mL, 25.6 mmol) and benzonitrile (1.390 mL, 13.48 mmol) at 0° C. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with ice, extracted with dichloromethane, and then purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compounds.

Aufarbeitung

  1. customThe reaction mixture was quenched with ice
  2. extractionextracted with dichloromethane
  3. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-02b4a6db30ed4228a49b78bcd09d1aba
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796470B2

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