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

HRID 249647

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

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).

Workup

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

Sources & evidence

ORD record: ord-8eb69558707c4d61a51dd21de84d5560
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863081B2

Linked notes

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