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

HRID 2423384Notes

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 mixed solution 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 a nitrogen gas, and 2.425 (22 mmol) of ethyl isocyanoacetate was added to the system, which was then cooled to 0° C. After dropping potassium t-butoxide (50 ml/1M THF solution) over 2 hours, the solution was stirred for 3 hours. After the reaction was finished, dilute hydrochloric acid was added to the solution. The reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate, 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, 16 mmol, yield 80%).

Workup

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

Sources & evidence

ORD record: ord-2cdbebd73095498faa56a610f9838e2f
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960716B2

Reaction notes

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