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

HRID 2115635Notes

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 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 solution, and the mixture was cooled to 0° C. Potassium t-butoxide (50 ml/1 M tetrahydrofuran (THF) solution) was dropped over 2 hours, and the whole was stirred at room temperature for 3 hours. After the completion of the reaction, dilute hydrochloric acid was added, and then the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, distilled water, and a saturated salt solution in this order, followed by drying with anhydrous sodium sulfate. The dried product was purified by 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).

Workup

additionwas added
washthe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
distillationdistilled water
dry with materialby drying with anhydrous sodium sulfate
customThe dried product was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record: ord-28fc5ce90dce47c0b12eafaa497a3604
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435989B2

Reaction notes

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