Reaktion #1995

Reaktionsgleichung

water

di-t-butyl malonate

NaH

8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

→

title compound

1-cyclopropyl-8-(diphenylmethoxycarbonylmethyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.ADDITIONabove is added
3. 3
   TemperaturThe reaction is then heated to 50° to 60° C.
4. 4
   ExtraktionThe product is extracted into methylene chloride
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeThe residue, after removal of the solvent
7. 7
   workup.DISSOLUTIONis dissolved in methylene chloride
8. 8
   Sonstigeat room temperature
9. 9
   SonstigeThe solvent is removed under vacuum
10. 10
    workup.ADDITIONthe product is treated with diphenyldiazomethane in methylene chloride and methanol
11. 11
    Sonstigethe solvents are removed under vacuum
12. 12
    Sonstigethe product is purified by column chromatography

Vorschrift

To a suspension of NaH in DMF with ice bath cooling is added di-t-butyl malonate. After the addition, 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester from Example 253i above is added. The reaction is then heated to 50° to 60° C., and the mixture is poured into water and acidified. The product is extracted into methylene chloride and dried over MgSO4. The residue, after removal of the solvent, is dissolved in methylene chloride and trifluoroacetic acid at room temperature. The solvent is removed under vacuum, and the product is treated with diphenyldiazomethane in methylene chloride and methanol. When the reaction is finished, the solvents are removed under vacuum, and the product is purified by column chromatography to give the title compound.

Quelle