反応 #1995

反応方程式

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

溶媒

DMF

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.ADDITIONabove is added
3. 3
   温度The reaction is then heated to 50° to 60° C.
4. 4
   抽出The product is extracted into methylene chloride
5. 5
   乾燥dried over MgSO4
6. 6
   その他The residue, after removal of the solvent
7. 7
   workup.DISSOLUTIONis dissolved in methylene chloride
8. 8
   その他at room temperature
9. 9
   その他The solvent is removed under vacuum
10. 10
    workup.ADDITIONthe product is treated with diphenyldiazomethane in methylene chloride and methanol
11. 11
    その他the solvents are removed under vacuum
12. 12
    その他the product is purified by column chromatography

実験手順

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.

出典