p-Toluenesulfonic acid monohydrate → Ethyl 2-(1,3-dioxo-1,3,4,5,6,7-hexahydro-isoindol-2-ylmethyl)-3-oxo-butyrate

HRID 10884

Reaktionsgleichung

[O:1]=[C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:19]1([CH3:24])OCC[O:20]1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[O:1]=[C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:19](=[O:20])[CH3:24])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Ethyl 3-(1,3-dioxo-1,3,4,5,6,7-hexahydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (866 mg, 2.57 mmol) was dissolved in a a solvent mixture of acetone/water (v/v=5/1), and a catalytic amount of p-toluenesulfonic acid monohydrate (190 mg, 0.76 mmol) was then added to the obtained solution. The resulting mixture was then refluxed at 80° C. for 4 days. After the reaction was completed, the reaction mixture where white solid were formed was washed with water. Acetone was removed by a vacuum evaporation, and the residue was extracted with dichloromethane. The combined organic layer was dried with anhydrous sulfate and then distilled under a reduced pressure in order to remove dichloromethane. The desired product was obtained (421 mg, 56%) by performing column chromatography (eluent: n-hexane/ethyl acetate=3/1). Rf=0.54 (eluent: n-hexane/ethyl acetate=1/1)

Aufarbeitung

customthe reaction mixture where white solid were formed
washwas washed with water
customAcetone was removed by a vacuum evaporation
extractionthe residue was extracted with dichloromethane
dry with materialThe combined organic layer was dried with anhydrous sulfate
distillationdistilled under a reduced pressure in order
customto remove dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-d7980a10b9df46969fa9c65469c6ee48
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07094908B2

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