Pyrrolidine, 1-[(2S)-2-pyrrolidinylcarbonyl]- (9CI) Chemical Properties

Boiling point:

320.2±35.0 °C(Predicted)

Density 

1.108±0.06 g/cm3(Predicted)

pka

9.24±0.10(Predicted)

Pyrrolidine, 1-[(2S)-2-pyrrolidinylcarbonyl]- (9CI) Usage And Synthesis

Application

1-[(2S)-2-pyrrolidinecarbonyl]-pyrrolidine (5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde) is mainly used in the synthesis of vonoprazan fumarate, a potassium-competitive acid blocker developed by Takeda Pharmaceutical Company of Japan for the treatment of erosive esophagitis, gastric ulcers, duodenal ulcers, and Helicobacter pylori eradication. It was launched in Japan on December 26, 2014. The synthesis is as follows: using 1-[(2S)-2-pyrrolidinecarbonyl]-pyrrolidine (5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde) as the raw material, tetrahydrofuran as the solvent, sodium hydride as the acid-binding agent, and crown ether as the phase transfer catalyst, it reacts with 3-pyridinesulfonyl chloride to obtain the intermediate 5-(2-fluorophenyl)-1-(pyridine-3-ylsulfonyl)-1H-pyrrole-3-carboxaldehyde, which then forms a Schiff base with methylamine, is reduced with sodium borohydride to obtain the free base of vonorazan, and then forms a salt with fumaric acid to generate vonorazan fumarate.

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