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

HRID 249647

反応式

HRID 249647 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

A reaction system of a mixed solution of 7.76 g (20 mmol) of the resultant 5,6-bis(phenylsulfonyl)-bicyclo[2,2,2]octa-2-ene and 50 ml of anhydrous tetrahydrofuran was replaced with nitrogen. Then, 2.425 ml (22 mmol) of ethyl isocyanoacetate were added to the mixed solution, and the whole was cooled to 0° C. Potassium tert-butoxide (50 ml/l M THF solution) was dropped into the mixture in 2 hours, and the whole was stirred at room temperature for 3 hours. After the completion of the reaction, diluted hydrochloric acid was added to the reaction mixture. Then, the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, distilled water, and a saturated aqueous solution in this order, and was dried with anhydrous sodium sulfate. The dried product was purified by means of silica gel column chromatography (chloroform) to yield ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate (3.5 g, 16 mmol, 80% yield).

後処理

  1. additionwas added to the reaction mixture
  2. washThen, the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. distillationdistilled water
  4. dry with materiala saturated aqueous solution in this order, and was dried with anhydrous sodium sulfate
  5. customThe dried product was purified by means of silica gel column chromatography (chloroform)

出典と根拠

ORDレコード
ord-8eb69558707c4d61a51dd21de84d5560
出典データセット
uspto-grants-2011_01
特許番号
US07863081B2

関連ノート

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