(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran

Physical Form

Solid

Uses

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran(915095-94-2) can be used as reactant/reagent in preparation of C-?aryl D-?glurofuranoside compounds useful as reference compounds in the quality control of gliflozin type medicine.

Description

(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran is a pharmaceutical intermediate compound that is used in the preparation of empagliflozin. Empagliflozin is an inhibitor of sodium-glucose co-transporter protein-2 (SGLT2), which is used in the treatment of type 2 diabetes.

Preparation

0.5 mol of (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone and 0.6 mol of aluminum chloride were added to 2 mol of methanol at a temperature of 20° C, and then 0.6 mol of triethylsilane was added to the mixed solution. The mixture was stirred at 25° C for 1 h.The conversion is determined by HPLC analysis. After the reaction is complete, it is extracted and distilled under reduced pressure.Finally, (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan (also known as (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran) was obtained through purification.