Description

(2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate (CAS No. 203866-16-4) is a high-purity fluorinated pyrrolidine derivative, widely utilized in pharmaceutical research and organic synthesis. With the molecular formula C₁₁H₁₈FNO₄, this chiral compound features a stereospecific (2S,4S) configuration, making it an essential building block for the development of bioactive molecules and peptidomimetics. The presence of both tert-butyl and methyl ester protecting groups enhances its stability and reactivity in multi-step synthetic routes. This product is rigorously tested for purity (typically ≥95% by HPLC or GC) and is supplied under inert conditions to ensure optimal shelf life. Ideal for medicinal chemistry, asymmetric catalysis, and fluorination studies.

Properties

• CAS Number: 203866-16-4
• Complexity: 313
• IUPAC Name: O1-tert-butyl O2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate
• InChI: InChI=1S/C11H18FNO4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6H2,1-4H3/t7-,8-/m0/s1
• InChI Key: METPQQHVRNLTRX-YUMQZZPRSA-N
• Exact Mass: 247.12198622
• Molecular Formula: C11H18FNO4
• Molecular Weight: 247.26
• SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)OC)F
• Topological: 55.8
• Monoisotopic Mass: 247.12198622
• Synonyms: 203866-16-4, (2S,4S)-1-TERT-BUTYL 2-METHYL 4-FLUOROPYRROLIDINE-1,2-DICARBOXYLATE, N-Boc-cis-4-Fluoro-L-proline methyl ester, 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate, 1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-, 1-O-tert-butyl 2-O-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate, 475561-81-0, MFCD11054130, SCHEMBL91557, METPQQHVRNLTRX-YUMQZZPRSA-N, N-(tert-Butoxycarbonyl)-(2S,4S)-4-fluoroprolinemethylester, AKOS005259523, AKOS016008665, CS-W001496, FB86441, DS-16715, A4437, EN300-7349843, N-Boc-cis-4-Fluoro-L-proline methyl ester, 97%, N-T-BOC-CIS-4-FLUORO-L-PROLINE METHYL ESTER, Ethyl (2S,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate, 1-tert-butyl 2-methyl (2S,4S)-4-fluoro-1,2-pyrrolidinedicarboxylate, methyl(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylate

Application

This compound serves as a versatile intermediate in the synthesis of fluorinated pharmaceuticals, particularly protease inhibitors and chiral ligands. Its rigid pyrrolidine scaffold and fluorine substituent are valuable for modulating metabolic stability and binding affinity in drug candidates. Researchers also employ it in peptide backbone modifications to enhance conformational control. Suitable for nucleophilic substitution or deprotection reactions under mild conditions.

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