1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate

HRID 1109565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109565
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[O:15]=[C:16]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[CH:24][C:23](C(O)=O)=[C:22]2[N:17]1[CH2:18][CH2:19][C:20]1[CH:38]=[CH:37][S:36][C:21]=12>C1(C)C=CC=CC=1>[F:32][C:28]1[CH:27]=[C:26]([C:25]2[C:16](=[O:15])[N:17]3[C:22](=[C:23]([C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])[CH:24]=2)[C:21]2[S:36][CH:37]=[CH:38][C:20]=2[CH2:19][CH2:18]3)[CH:31]=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 19020416HCID 19020416, Verbindung

Produkt 1

HCID 19020443tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.96 ml of N,N-dimethylformamide di-t-butyl acetal was added dropwise within 20 minutes to a boiling solution of 0.34 g of 4,5-dihydro-7-oxo-8-(m-fluorophenyl)-7H-thieno[2,3-a]quinolizine-10-carboxylic acid in 5 ml of toluene. The mixture was heated under reflux for an additional 30 minutes, left to stand at room temperature overnight and then washed once with water, twice with saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate and there was obtained tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a ]quinolizine-10-carboxylate of m.p. 135°-137°.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for an additional 30 minutes
  3. waitleft
  4. washwashed once with water, twice with saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3922151c0c1f482aac5b71db6122eae0
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05321021

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