Name: Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

D-Proline, 4-hydroxy-, methyl ester hydrochloride; (2R,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate HCl; 4-(R)-Hydroxypyrrolidine-2-(R)-carboxylic acid methyl ester hydrochloride

IUPAC Name

methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride

Canonical SMILES

COC(=O)C1CC(CN1)O.Cl

InChI

InChI=1S/C6H11NO3.ClH/c1-10-6(9)5-2-4(8)3-7-5;/h4-5,7-8H,2-3H2,1H3;1H/t4-,5-;/m1./s1

InChIKey

KLGSHNXEUZOKHH-TYSVMGFPSA-N

Melting Point

121-123°C

Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride, a chiral amino acid derivative, has various applications in chemical synthesis and pharmaceutical development. Here are some key applications of this compound:

Chiral Synthesis: This compound is often used as a chiral building block in organic synthesis, facilitating the creation of optically active compounds. Its specific stereochemistry is beneficial for producing molecules with precise three-dimensional arrangements, crucial for the efficacy of pharmaceuticals. By incorporating Methyl (2R4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride, chemists can develop enantiomerically pure drugs and fine chemicals.

Pharmaceutical Development: In drug discovery, this compound serves as an intermediate in the synthesis of various therapeutic agents, particularly those targeting neurotransmitter pathways. Its role in the synthesis of compounds acting on the central nervous system highlights its importance in developing treatments for neurological disorders. The compound’s structure provides a foundation for designing derivatives with enhanced pharmacological properties.

Catalysis: The compound can also be used in catalytic processes where it acts as a chiral ligand or auxiliary in asymmetric reactions. This is vital for generating high yields of enantiomerically enriched products, which is a significant advantage in manufacturing pharmaceuticals. Its effectiveness in asymmetric synthesis aids in the exploration of innovative catalytic methodologies.

Research on Mechanistic Pathways: Methyl (2R4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride is useful in studying mechanistic pathways in biochemical reactions involving pyrrolidine derivatives. By observing how this compound interacts in various reactions, researchers can elucidate aspects of enzymatic and non-enzymatic pathways. This understanding contributes to advancements in both theoretical and applied aspects of chemical research.