Description

(2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate (CAS: 203866-18-6) is a highly specialized fluorinated pyrrolidine derivative, widely utilized in pharmaceutical research and organic synthesis. This compound features a stereochemically defined (2S,4R) configuration, ensuring precise reactivity in chiral environments. The presence of both tert-butyloxycarbonyl (Boc) and methyl ester protecting groups enhances its stability and compatibility with diverse synthetic protocols. With a molecular formula of C₁₁H₁₈FNO₄, it is particularly valuable for constructing fluorinated amino acid analogs and peptidomimetics. Packaged under inert conditions to guarantee purity, this reagent is ideal for medicinal chemistry, asymmetric catalysis, and the development of bioactive molecules.

Properties

• CAS Number: 203866-18-6
• Complexity: 313
• IUPAC Name: O1-tert-butyl O2-methyl (2S,4R)-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+/m1/s1
• InChI Key: METPQQHVRNLTRX-SFYZADRCSA-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: 203866-18-6, (2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate, N-BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER, 1-tert-butyl 2-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate, 1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4R)-, 1-O-tert-butyl 2-O-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate, (4R)-1-Boc-4-Fluoro-L-proline methyl ester, BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER, MFCD07367993, 1648910-85-3, SCHEMBL2995724, DTXSID00473199, METPQQHVRNLTRX-SFYZADRCSA-N, Methyl N-(tert-butoxycarbonyl)-(2S, 4R)-4-fluoroprolinate, AKOS015961653, CS-W012681, FB50550, AC-14451, AC-33231, AS-36306, EN300-7282689, N-Boc-trans-4-fluoro-L-proline methyl ester, 97%, Methyl (2S,4R)-1-Boc-4-fluoropyrrolidine-2-carboxylate, (2S,4R)-2-methyl N-Boc-4-fluoro-pyrrolidine-2-carboxylate, (2S,4R)-4-FLUOROPYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL 2-METHYL DIESTER, 1,2-Pyrrolidinedicarboxylicacid,4-fluoro-,1-(1,1-dimethylethyl)2-methyl ester,(2S,4R)-

This compound serves as a critical intermediate in the synthesis of fluorinated proline derivatives, which are pivotal in peptide-based drug discovery. Its robust Boc and methyl ester protections enable selective deprotection strategies for stepwise synthesis. Researchers leverage its stereochemistry to modulate peptide conformation and enhance metabolic stability. It is also employed in the preparation of fluorinated ligands for asymmetric catalysis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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