ethyl (2S,5S)-5-methylpyrrolidine-2-carboxylate(CAS: 676560-84-2)

Ethyl (2S,5S)-5-methylpyrrolidine-2-carboxylate is a colorless to slightly yellow liquid with a molecular weight of approximately 174.26 g/mol. It is slightly soluble in water but miscible with organic solvents like ethanol and acetone. This compound exhibits basic behavior due to the carboxylate group and shows reactivity towards nucleophiles. It has a pKa of around 4.5 and can form salts with acids.

Ethyl (2S,5S)-5-methylpyrrolidine-2-carboxylate is typically synthesized via the reaction of pyrrolidine-2-carboxylic acid with ethyl chloroformate followed by reduction of the acyl chloride. The reaction involves the use of a phase transfer catalyst in the presence of a base like triethylamine. The yield is usually around 70-80%, depending on the purification method.

Ethyl (2S,5S)-5-methylpyrrolidine-2-carboxylate is used in the pharmaceutical industry for the synthesis of drugs, particularly those requiring chiral intermediates. It is also utilized in the polymer industry for the preparation of polymeric materials and in the sensor industry for the development of gas sensors. Its use in semiconductor manufacturing for etching and cleaning processes is also reported.

When handling ethyl (2S,5S)-5-methylpyrrolidine-2-carboxylate, it is essential to wear appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. Work should be conducted in a fume hood to minimize inhalation exposure. Spills should be contained and cleaned up using absorbent materials, followed by proper disposal. Safety data sheets (SDS) should be consulted for detailed handling and emergency procedures. It is also important to ensure the product is stored in a cool, dry place away from strong acids and bases.