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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 868314Generated: October 30, 2026

Sulfuric Acid → (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione

https://huagongshe.com/reaction/868314

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSulfuric AcidHCID 1118—
ReactantDichloromethaneHCID 6344—
Reactant(S)-alpha-Ethyl-1,1-(ethylenedioxy)-alpha-hydroxy-6-(hydroxymethyl)-N-[(R)-1-phenylethyl]-5-oxo-1,2,3,5-tetrahydroindolizine-7-acetamideHCID 11133734—
Solvent1,2-DimethoxyethaneHCID 8071—
Product(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trioneHCID 1022090062.9%

Reaction Steps

Dissolved in 15 ml of dimethoxyethane was 815 mg of the compound (VI) obtained in the above procedure (1), followed by an addition of 5 ml of 2N H2SO4. The thus-prepared solution was heated with stirring for 20 hours under a nitrogen gas stream. After completion of the reaction, 150 ml of dichloromethane was added and the resultant mixture was washed with water. The organic layer was then dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized from a mixed solvent of ethanol and petroleum ether to obtain 315 mg of the title compound as colorless needle-like crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04778891
Source datasetuspto-grants-1988_10
ORD IDord-107818bd1ed84e0eab1f153f6d1c60b1
Source noteuspto-grants-1988_10