Diethyl (ethoxymethylene)malonate → Ethyl 2-[(3-chlorophenyl)methyl]-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylate

HRID 747845ノート

反応式

HRID 747845 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][C:7]1=[O:12].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]2[CH:26]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([OH:18])=[C:8]2[C:7]1=[O:12]

参加物

6

反応物 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 200992811-[(3-Chlorophenyl)methyl]piperazin-2-one

生成物 1

HCID 3011073Ethyl 2-[(3-chlorophenyl)methyl]-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(3-chlorobenzyl)piperazin-2-one (3.97 g, 17.67 mmol) and diethyl ethoxymethylenemalonate (4.01 g, 18.55 mmol) in toluene (60 mL) was heated in a sealed tube at 80° C. overnight. The resultant mixture was concentrated under vacuum. The residue was dissolved in anhydrous DMF (200 mL), cooled to 0° C. under an atmosphere of nitrogen, and treated with a solution of lithium bis(trimethylsilyl)amide in THF (1 M, 21.2 mL, 21.2 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under vacuum. The residue was partitioned between ethyl acetate and dilute aqueous HCl. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated with diethyl ether, and the solid precipitated was filtered to provide the title compound.

後処理

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in anhydrous DMF (200 mL)
  3. temperaturecooled to 0° C. under an atmosphere of nitrogen
  4. concentrationconcentrated under vacuum
  5. customThe residue was partitioned between ethyl acetate and dilute aqueous HCl
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe residue was triturated with diethyl ether
  12. customthe solid precipitated
  13. filtrationwas filtered

出典と根拠

ORDレコード
ord-6202238b26b741f7b5527e19df42f912
出典データセット
uspto-grants-2008_07
特許番号
US07399763B2

反応ノート

読み込み中…