methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate → methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927920
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:18]C(=O)C(C)(C)C)[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]>S(=O)(=O)(O)O.CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:18])[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 86713286methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate2×

Produkt 1

HCID 86713285methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Concentrated sulfuric acid (5 drops) was added to a solution of methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 30, 0.15 g) in methanol (5 mL) and the solution was stirred and heated at reflux for 48 hours. After cooling, the mixture was evaporated to low volume and the residue was dissolved in ethyl acetate and carefully washed with saturated aqueous sodium bicarbonate solution. The organic layer was filtered through a phase separator and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (0.09 g) as a brown gum.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to low volume
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washcarefully washed with saturated aqueous sodium bicarbonate solution
  7. filtrationThe organic layer was filtered through a phase separator
  8. customthe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f54dc18af68f404f882cf295af3eba88
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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