Description

(2R,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (CAS No. 681128-50-7) is a high-purity fluorinated pyrrolidine derivative widely utilized in pharmaceutical research, medicinal chemistry, and peptide synthesis. With the molecular formula C₁₀H₁₆FNO₄, this chiral compound serves as a critical building block for the development of bioactive molecules, particularly in the synthesis of protease inhibitors and other therapeutic agents. The tert-butoxycarbonyl (Boc) protecting group enhances stability during synthetic processes, while the fluorinated pyrrolidine core contributes to improved metabolic stability and binding affinity in drug candidates. This product is supplied as a white to off-white crystalline powder, rigorously characterized by HPLC, NMR, and mass spectrometry to ensure ≥95% purity. Store at 2-8°C in a tightly sealed container under inert conditions to maintain optimal stability.

Properties

• CAS Number: 681128-50-7
• Complexity: 300
• IUPAC Name: (2R,4S)-1-tert-butoxycarbonyl-4-fluoro-pyrrolidine-2-carboxylic acid
• InChI: InChI=1S/C10H16FNO4/c1-10(2,3)16-9(15)12-5-6(11)4-7(12)8(13)14/h6-7H,4-5H2,1-3H3,(H,13,14)/t6-,7+/m0/s1
• InChI Key: YGWZXQOYEBWUTH-NKWVEPMBSA-N
• Exact Mass: 233.10633615
• Molecular Formula: C10H16FNO4
• Molecular Weight: 233.24
• SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@@H]1C(=O)O)F
• Topological: 66.8
• Monoisotopic Mass: 233.10633615
• Synonyms: 681128-50-7, (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid, DTXSID30433145, DTXCID70383973, 826-472-5, (4S)-1-Boc-4-fluoro-D-proline, (2R,4S)-4-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid, MFCD08706411, N-Boc-(4S,2R)-4-fluoro-2-pyrrolidinecarboxylic acid, (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylic acid, C10H16FNO4, SCHEMBL1853822, (2R,4S)-1-tert-butoxycarbonyl-4-fluoro-pyrrolidine-2-carboxylic acid, AKOS015898027, DS-5551, HY-W021482, CS-0040722, EN300-154319, P10646, (2R,4S)-1-(Boc)-4-fluoropyrrolidine-2-carboxylic acid, Z1505702390, (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylicacid, (2R,4S)-4-Fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

This compound is primarily employed as a key intermediate in the synthesis of fluorinated peptidomimetics and protease inhibitors, particularly for targeting viral or enzymatic pathways. Its rigid pyrrolidine scaffold and fluorine substitution make it valuable for modulating conformational stability and bioactivity in drug discovery. Researchers also use it in asymmetric synthesis and as a chiral auxiliary in stereoselective reactions. Suitable for solid-phase peptide synthesis (SPPS) and solution-phase applications.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• 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, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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