Sulfuric Acid → 5-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole

HRID 243629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243629
S(=O)(=O)(O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C@@H:19]([CH2:27]O)[C@H:18]([CH2:29][NH:30][CH:31]=O)[C:17]=2[CH:33]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[CH:19]3[CH2:27][N:30]([CH3:31])[CH2:29][CH:18]3[C:17]=2[CH:33]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 56652273HCID 56652273, Verbindung

Produkt 1

HCID 99039705-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Concentrated sulfuric acid (618 mg, 6.3 mmol) is added carefully at −10° C. to a suspension of lithium aluminum hydride (478 mg, 12.6 mmol) in dry THF (20 mmol). Then a solution of (6) (1.0 g, 3.1 mmol) in THF (5 mL) is added dropwise and the mixture stirred at 40° C. for 6 hr. After quenching sequentially with H2O (0.5 mL), 15% NaOH (0.5 mL) and H2O (1.5 mL), the white precipitate is filtered and the filtrate evaporated. The residue is purified by flash chromatography (Heptane:Ethyl Acetate 7:3) giving 612 mg (69%) of trans-(5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz[2,3:6,7]oxepino-[4,5-c]pyrrole (Asenapine) as a slightly yellow oil.

Aufarbeitung

  1. customAfter quenching sequentially with H2O (0.5 mL), 15% NaOH (0.5 mL) and H2O (1.5 mL)
  2. filtrationthe white precipitate is filtered
  3. customthe filtrate evaporated
  4. customThe residue is purified by flash chromatography (Heptane:Ethyl Acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-a11fcfb443264910b64e6e19364a8360
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653280B2

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