951382-34-6

Ipragliflozin (L-Proline) is a highly potent and selective SGLT2 inhibitor with an IC50 of 2.8 nM; little and NO potency for SGLT1/3/4/5/6.

Synthesis of (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol and L-proline as raw materials for the synthesis of (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-( hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (S)-pyrrolidine-2-carboxylate was prepared in the following general procedure: in a dichloromethane solvent, 24.65 g (61.02 mmol)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol was added. pyran-3,4,5-triol and 7.02 g (61.02 mmol) of L-proline. The reaction mixture was heated to 35°C and stirred at this temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the crude product was collected by filtration. The crude product was purified by recrystallization from methanol to give 31.35 g of the target product, i.e., (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophene-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (S)- pyrrolidine-2- carboxylate, with a purity of 99.8% and a yield of 99%.

SGLT2

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