(R)-4-Hydroxypyrrolidin-2-one, CAS No. 22677-21-0

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22677-21-0

Catalog No. EBD2199025

CAS 22677-21-0

Name (R)-4-Hydroxypyrrolidin-2-one

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Basic Information

Synonyms: (R)-4-Hydroxypyrrolidin-2-one (R)-4-hydroxy-2-pyrrolidone (R)-(+)-4-Hydroxy-2-pyrrolidone (R)-(+)-4-Hydroxy-2-pyrrolidinone (4R)-4-hydroxypyrrolidin-2-one

Molecular Formula: C4H7NO2

Molecular Weight: 101.1

MDL Number: MFCD00273364

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

(R)-4-Hydroxy-2-pyrrolidone is a chiral heterocyclic compound featuring a five-membered lactam ring with a hydroxyl group at the 4-position. It serves as a crucial chiral building block in organic synthesis, particularly for the preparation of biologically active molecules. This compound is a key intermediate in the synthesis of various pharmaceuticals and natural products. Its primary application lies in the production of carbapenem antibiotics, a class of broad-spectrum β-lactam antibiotics. The chiral (R)-configuration of the hydroxyl group is essential for imparting the desired biological activity to the final drug molecules. It is also utilized in the synthesis of other complex targets, including pyrrolidine alkaloids and peptide mimetics. As a versatile synthon, (R)-4-hydroxy-2-pyrrolidone is valued for its ability to introduce both the pyrrolidone scaffold and a handle for further functionalization. It is typically handled under inert atmosphere and stored at low temperatures to maintain stability.

Physical Properties

Melting Point: 156-159 °C(lit.)

Boiling Point: 363.6 °C at 760 mmHg

Flash Point: 173.7 °C

Density: 1.292 g/cm3

Analytical Data

Appearance: white to light yellow crystal powder