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Ethyl Acetate → 3-Ethyl-2,3,9,10,11,12-hexahydro-1-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate

HRID 1195783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195783
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([CH:13]1[C:19](=[O:20])[N:18]([CH3:21])[C:17]2=[C:22]3[C:27](=[N:28][C:29]4=[CH:30][CH:31]=[CH:32][C:15](=[C:16]24)[O:14]1)[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:12].[OH-:33].[Na+].[C:35]([O:38]CC)(=[O:37])[CH3:36]>O1CCCC1>[C:19]([OH:20])(=[O:33])/[CH:13]=[CH:36]/[C:35]([OH:38])=[O:37].[CH2:11]([CH:13]1[CH2:19][N:18]([CH3:21])[C:17]2=[C:22]3[C:27](=[N:28][C:29]4=[CH:30][CH:31]=[CH:32][C:15](=[C:16]24)[O:14]1)[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 538029823-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Produkt 1

HCID 67756603
3-Ethyl-2,3,9,10,11,12-hexahydro-1-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate
Ausbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 11.99 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.6 g) in portions, with stirring. After five mins, 3-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (3.55 g) was added, and stirring was continued for 0.5 hr. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added, the organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (1.5% triethylamine/toluene). The appropriate fractions were concentrated and the residue was treated with fumaric acid followed by recrystallization from methanol to give 1.82 g (38%) of product, mp 243° C. (dec.).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 0.5 hr
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (1.5% triethylamine/toluene)
  8. concentrationThe appropriate fractions were concentrated
  9. additionthe residue was treated with fumaric acid
  10. customfollowed by recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5c88cfaa295d4ff1b9ae13cfd4e6fb0b
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112829

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