Description

1-O-tert-butyl 2-O-methyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate (CAS No. 130966-46-0) is a high-purity chiral pyrrolidine derivative with the molecular formula C₁₁H₁₉NO₅. This compound features a stereochemically defined hydroxy group at the 3-position, making it a valuable intermediate in asymmetric synthesis and pharmaceutical research. The tert-butyl and methyl ester moieties enhance its stability and reactivity, enabling applications in peptide mimetics, organocatalysis, and medicinal chemistry. Supplied as a white to off-white crystalline solid, it is rigorously characterized by HPLC, NMR, and mass spectrometry to ensure ≥95% purity. Ideal for researchers developing protease inhibitors, chiral ligands, or bioactive scaffolds.

Properties

• CAS Number: 130966-46-0
• Complexity: 309
• IUPAC Name: O1-tert-butyl O2-methyl (2S,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-SFYZADRCSA-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: 1449588-26-4, 1,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-, 130966-46-0, (2S,3R)-1-tert-Butyl 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate, 1-tert-butyl 2-methyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, (2S,3R)-1-(tert-BOC)-3-Hydroxypyrrolidine-2-carboxylic acid methyl ester, 1-O-tert-butyl 2-O-methyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, 1,2-PYRROLIDINEDICARBOXYLIC ACID, 3-HYDROXY-, 1-(1,1-DIMETHYLETHYL) 2-METHYL ESTER, (2S,3R)-, (2S,3R)-1-TERT-BUTYL-2-METHYL-3-HYDROXYPYRROLIDINE-1,2-DICARBOXYLATE, MFCD13248611, Rel-1-(tert-butyl) 2-methyl (2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate, (2S,3R)-N-TERT-BUTOXYCARBONYL-3-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID METHYL ESTER, SVSSZFBZFUSINI-SFYZADRCSA-N, SCHEMBL200978, DTXSID201116363, AKOS015920189, AS-43212, CS-0052392, (2s,3r)-3-hydroxy-N-boc-proline methyl ester, N-BOC-3(R)-hydroxy-(L)-proline, methyl ester, (2S,3R)-1-tert-Butyl2-methyl3-hydroxypyrrolidine-1,2-dicarboxylate, (2S,3R)-1-(Boc)-3-Hydroxypyrrolidine-2-carboxylic acid methyl ester, (2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester

Application

This compound serves as a versatile chiral building block for the synthesis of peptidomimetics and protease inhibitors, particularly in HIV and hepatitis C research. Its stereospecific hydroxy group enables diastereoselective transformations, while the ester functionalities allow for further derivatization. Used in organocatalysis to construct complex heterocycles with high enantiomeric excess. Also employed in medicinal chemistry for the design of CNS-active compounds due to its pyrrolidine core.

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