Triethylamine → 3-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl ester

HRID 909255ノート

反応式

HRID 909255 の反応式
C[CH:2]([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].[C:9]1([CH:15]2[NH:20][CH2:19][CH2:18][N:17]3[CH:21]=[CH:22][CH:23]=[C:16]23)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(CC)CC.C(Cl)(Cl)Cl.[C:35](OCC)(=[O:37])C>C(Cl)Cl>[CH3:35][O:37][C:6](=[O:7])[CH2:2][C:3](=[O:4])[N:20]1[CH2:19][CH2:18][N:17]2[CH:21]=[CH:22][CH:23]=[C:16]2[CH:15]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazineHCID 10931669MethylmalonylchlorideHCID 21584013Chloroform ethylacetate

生成物 1

HCID 674008753-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl ester収率 55%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (852 μl, 7.9 mmol) of methyl-malonyl chloride in DCM (5 ml) was added dropwise, with vigorous stirring and while cooling (ice-bath), to a solution of (1.5 g, 7.6 mmol) of 1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (A2) and (1.27 ml, 9.1 mmol) of NEt3 in DCM (35 ml). Stirring was then carried out for 60 min at RT. The mixture was then washed with water and brine, and the organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (chloroform/ethyl acetate 10:1) yielded 1.26 g (4.2 mmol, 55%) of 3-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl ester.

後処理

  1. temperaturewhile cooling (ice-bath)
  2. stirringStirring
  3. washThe mixture was then washed with water and brine
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-28db2bcd0eb444e0a9ee1d5866be6bc4
出典データセット
uspto-grants-2011_09
特許番号
US08017772B2

反応ノート

読み込み中…