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1-Boc-4-piperidylacetic acid
1-Boc-4-piperidylacetic acid (CAS 157688-46-5), also known as 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid, is a strategically protected piperidine-carboxylic acid derivative engineered for pharmaceutical intermediate synthesis, ligand development, and peptidomimetic construction. This molecule integrates a saturated piperidine core—with an acid-labile Boc (tert-butoxycarbonyl) protecting group on the nitrogen atom (N1-position)—and an acetic acid side chain at the C4 position. The N-Boc protection prevents unwanted N-alkylation during synthetic sequences and can be removed under mild acidic conditions, while the carboxylic acid terminus enables amide coupling, esterification, or salt formation for formulation optimization. Compared to its aminomethyl analog (CAS 144222-22-0), the acetic acid group provides direct access to amide/ester linkages with enhanced metabolic stability. Compared to its benzyl ester analog (CAS 177990-33-9), the free acid form offers immediate coupling capability without deprotection steps. This intermediate is particularly valuable for constructing CNS-active pharmaceuticals, GPCR ligands, peptidomimetics, and piperidine-based scaffolds where controlled nitrogen reactivity and carboxylic acid functionality are critical. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to differentially protected piperidine-carboxylic acid architectures.
Property
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Product Name
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1-Boc-4-piperidylacetic acid
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CAS Number
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157688-46-5
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Chinese Name
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1-Boc-4-哌啶基乙酸
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Synonyms
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2-(1-(tert-Butoxycarbonyl)piperidin-4-yl)acetic acid; N-Boc-piperidine-4-acetic acid; 1-Boc-piperidin-4-ylacetic acid; C₁₂H₂₁NO₄ protected acid
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Chinese Synonyms
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2-(1-叔丁氧羰基哌啶-4-基) 乙酸; N-Boc-哌啶-4-乙酸; 1-Boc-哌啶-4-基乙酸; Boc-哌啶乙酸
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Molecular Formula
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C₁₂H₂₁NO₄
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Molecular Weight
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243.30 g/mol
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Purity
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≥ 98% (HPLC area normalization)
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Product Category
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Pharmaceutical Intermediates / Piperidine Derivatives / Protected Carboxylic Acids
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Appearance
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Yellow to brown Crystalline Powder or Solid
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Melting Point
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~110-115°C (literature reference recommended)
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pKa
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~4.0-5.0 (carboxylic acid, estimated); ~9.5-10.0 (Boc-protected amine, non-basic)
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Storage Conditions
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Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong acids to avoid premature Boc deprotection and from strong bases to avoid salt formation.
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Shelf Life
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18-24 months under recommended storage conditions
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Packaging
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100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
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Applications
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CNS drug synthesis (GPCR ligands), peptidomimetic development, piperidine-based ligand construction, amide coupling for drug conjugates, esterification for prodrug design, heterocyclic library synthesis
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Reactivity
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Suitable for selective Boc deprotection (TFA/HCl), carboxylic acid activation (EDC/HATU/DCC), esterification, amide coupling, salt formation, and sequential functionalization
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Special Note
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✅ Orthogonally Protected Acid Scaffold—N-Boc enables selective carboxylic acid modification before amine deprotection. Distinct from aminomethyl analog (CAS 144222-22-0) by acid vs. amine functionality. Distinct from benzyl ester (CAS 177990-33-9) by direct coupling capability. Part of our protected piperidine building block series.
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