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

HRID 732321Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-ceb984c1462c428aa479ebf92d868891
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07586117B2

Reaction notes

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