Description

(S)-Bis(4-methoxyphenyl)(pyrrolidin-2-yl)methanol (CAS No. 131180-57-9) is a high-purity chiral compound with the molecular formula C₁₉H₂₃NO₃. This optically active pyrrolidine derivative features two 4-methoxyphenyl groups and a hydroxymethyl substituent on the pyrrolidine ring, making it a valuable intermediate for asymmetric synthesis and pharmaceutical research. Its stereochemical purity (>98% ee) ensures consistent performance in enantioselective reactions. The compound is supplied as a white to off-white crystalline solid with a melting point range of 120-125°C and is soluble in common organic solvents (DMSO, methanol, chloroform). Suitable for use under inert atmosphere, this product is rigorously characterized by ¹H/¹³C NMR, HPLC, and mass spectrometry to guarantee structural integrity. Packaged in amber glass vials with argon protection to prevent degradation.

Properties

• CAS Number: 131180-57-9
• Complexity: 336
• IUPAC Name: bis(4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methanol
• InChI: InChI=1S/C19H23NO3/c1-22-16-9-5-14(6-10-16)19(21,18-4-3-13-20-18)15-7-11-17(23-2)12-8-15/h5-12,18,20-21H,3-4,13H2,1-2H3/t18-/m0/s1
• InChI Key: DIHSOOPDCJLLHA-SFHVURJKSA-N
• Exact Mass: 313.16779360
• Molecular Formula: C19H23NO3
• Molecular Weight: 313.4
• SMILES: COC1=CC=C(C=C1)C([C@@H]2CCCN2)(C3=CC=C(C=C3)OC)O
• Topological: 50.7
• Monoisotopic Mass: 313.16779360
• Synonyms: 131180-57-9, (S)-ALPHA,ALPHA-BIS(4-METHOXYPHENYL)-2-PYRROLIDINEMETHANOL, (S)-Bis(4-methoxyphenyl)(pyrrolidin-2-yl)methanol, 2-Pyrrolidinemethanol, alpha,alpha-bis(4-methoxyphenyl)-, (2S)-, bis(4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methanol, MFCD08702731, SCHEMBL9226010, 2-Pyrrolidinemethanol, a,a-bis(4-methoxyphenyl)-, (2S)-, AS-77109, CS-0085699, D95532, 2-Pyrrolidinemethanol,a,a-bis(4-methoxyphenyl)-,(2S)-, 2-Pyrrolidinemethanol, ?,?-bis(4-methoxyphenyl)-, (2S)-, (S)-alpha,alpha-Bis(4-methoxy-phenyl)-2-pyrrolidinemethanol

This compound serves as a key chiral building block for the synthesis of biologically active molecules, particularly in developing CNS-targeting pharmaceuticals. Researchers employ it as a ligand precursor for asymmetric catalysis in C-C bond forming reactions. The methoxy-substituted aromatic rings enhance electron density for metal coordination in transition state stabilization. In medicinal chemistry, the pyrrolidine core facilitates exploration of dopamine receptor modulators and enzyme inhibitors. Its stereocenter allows investigation of structure-activity relationships in drug discovery programs.

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