Hydrochloric Acid → 4,7-Ethano-2H-isoindole-1-carboxylic acid, 4,7-dihydro-, ethyl ester

HRID 732321

反応式

HRID 732321 の反応式
C1(S([CH:10]2[CH:15](S(C3C=CC=CC=3)(=O)=O)[CH:14]3[CH2:25][CH2:26][CH:11]2[CH:12]=[CH:13]3)(=O)=O)C=CC=CC=1.[N+:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[C-:28].CC(C)([O-])C.[K+].Cl>O1CCCC1>[CH2:33]([O:32][C:30]([C:29]1[NH:27][CH:28]=[C:15]2[C:10]=1[CH:11]1[CH2:26][CH2:25][CH:14]2[CH:13]=[CH:12]1)=[O:31])[CH3:34]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 533707Ethyl isocyanoacetateHCID 127784115,6-Di(benzenesulfonyl)bicyclo[2.2.2]oct-2-eneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 121166594,7-Ethano-2H-isoindole-1-carboxylic acid, 4,7-dihydro-, ethyl ester収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

The reaction system of a mixture liquid of 7.76 g (20 mmol) of the obtained 5,6-bis(phenylsulfonyl)-bicyclo[2.2.2]octa-2-ene and 50 ml of anhydrous tetrahydrofuran was purged with nitrogen, and 2.425 ml (22 mmol) of ethyl isocyanoacetate was added to the system then cooled to 0° C. After dropping potassium t-butoxide (50 ml/1 M THF solution) over 2 hours, the solution was stirred for 3 hours. After the reaction was finished, dilute hydrochloric acid was added. The reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate solution, distilled water and saturated saline, and dried over anhydrous sodium sulfate. The resulting product was purified using silica gel column chromatography (chloroform) to give ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate (3.5 g, 1.6 mmol, yield 80%).

後処理

  1. additionwas added to the system
  2. customover 2 hours
  3. washThe reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate solution
  4. distillationdistilled water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe resulting product was purified

出典と根拠

ORDレコード
ord-ceb984c1462c428aa479ebf92d868891
出典データセット
uspto-grants-2009_09
特許番号
US07586117B2

関連ノート

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