Description

1-Tert-butyl 2-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate (CAS: 2165775-01-7) is a high-purity chiral building block extensively used in pharmaceutical research and organic synthesis. With the molecular formula C₁₁H₁₉NO₅, this compound features a stereochemically defined (2R,3R)-3-hydroxypyrrolidine core protected by tert-butyl and methyl ester groups, making it an ideal intermediate for asymmetric synthesis. Its rigid pyrrolidine scaffold and hydroxyl functionality enable versatile applications in drug discovery, particularly for the development of bioactive molecules, peptidomimetics, and enzyme inhibitors. Supplied as a white to off-white crystalline solid with ≥95% purity (HPLC), this product is rigorously tested for consistency and stability, ensuring reliable performance in complex synthetic routes. Store under inert conditions at 2-8°C to maintain integrity.

Properties

• CAS Number: 2165775-01-7
• Complexity: 309
• IUPAC Name: O1-tert-butyl O2-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate
• InChI: InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-5-7(13)8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8-/m1/s1
• InChI Key: SVSSZFBZFUSINI-HTQZYQBOSA-N
• Exact Mass: 245.12632271
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.27
• SMILES: CC(C)(C)OC(=O)N1CC[C@H]([C@@H]1C(=O)OC)O
• Topological: 76.1
• Monoisotopic Mass: 245.12632271
• Synonyms: 2165775-01-7, 1-TERT-BUTYL 2-METHYL (2R,3R)-3-HYDROXYPYRROLIDINE-1,2-DICARBOXYLATE, rel-1-(tert-Butyl) 2-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, MFCD31537068, 1-O-Tert-butyl 2-O-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, SCHEMBL8304417, BS-43535, CS-0159345, P18282, 2-Methyl (2R,3R)-1-boc-3-hydroxypyrrolidine-2-carboxylate, 1-t-Butyl 2-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, 1-(tert-Butyl) 2-methyl (2R,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, 1-TERT-BUTYL2-METHYL(2R,3R)-3-HYDROXYPYRROLIDINE-1,2-DICARBOXYLATE

This compound serves as a key chiral synthon in the asymmetric synthesis of pharmaceutical agents, particularly for constructing pyrrolidine-based scaffolds found in protease inhibitors and receptor modulators. It is widely employed in medicinal chemistry for the preparation of enantiomerically pure intermediates, enabling the development of novel therapeutics. Researchers also utilize it in peptide mimicry and as a precursor for advanced glycoconjugates due to its reactive hydroxyl and carboxylate functionalities.

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