Benzyl n-boc-4-piperidinecarboxylate

Benzyl N-Boc-4-piperidinecarboxylate (CAS 177990-33-9), also known as 1-(tert-butoxycarbonyl)-4-(benzyloxycarbonyl)piperidine, is a strategically diprotected piperidine derivative engineered for pharmaceutical intermediate synthesis, combinatorial chemistry, and heterocyclic construction. This molecule integrates a saturated piperidine core with orthogonal protecting groups: an acid-labile Boc (tert-butoxycarbonyl) group on the nitrogen atom (N1-position) and a benzyl ester at the C4-position. The N-Boc protection prevents unwanted N-alkylation during synthetic sequences and can be removed under mild acidic conditions (TFA/HCl), while the benzyl ester can be selectively cleaved via hydrogenolysis (Pd/C, H₂) or strong acid treatment to liberate the carboxylic acid. This dual-protection architecture enables highly controlled sequential functionalization, allowing chemists to independently modify the nitrogen and C4-carboxyl positions. This intermediate is particularly valuable for constructing CNS-active pharmaceuticals, peptidomimetics, GPCR ligands, and piperidine-based scaffolds where orthogonal deprotection strategies are critical for multi-step synthesis. Manufactured under controlled conditions, it supports drug discovery programs requiring modular access to differentially protected piperidine architectures with defined reactivity patterns.

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Product Name	Benzyl N-Boc-4-piperidinecarboxylate
CAS Number	177990-33-9
Chinese Name	苯甲基 N-Boc-4-哌啶羧酸酯
Synonyms	1-Boc-4-(benzyloxycarbonyl)piperidine; Benzyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate; N-Boc-piperidine-4-carboxylic acid benzyl ester; C₁₈H₂₅NO₄ protected piperidine
Chinese Synonyms	1-Boc-4-(苄氧羰基)哌啶; 叔丁基 4-(苄氧基羰基)哌啶-1-羧酸酯; N-Boc-哌啶-4-羧酸苄酯; 双保护哌啶中间体
Molecular Formula	C₁₈H₂₅NO₄
Molecular Weight	319.40 g/mol
Purity	≥ 98% (HPLC area normalization)
Product Category	Pharmaceutical Intermediates / Piperidine Derivatives / Protected Amino Acid Esters
Appearance	White to Off-white Crystalline Powder or Solid
Melting Point	~65-69°C (literature reference recommended)
Storage Conditions	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 hydrogenation conditions to avoid benzyl ester cleavage.
Shelf Life	18-24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications	CNS drug synthesis (GPCR ligands), peptidomimetic development, piperidine-based ligand construction, combinatorial chemistry library synthesis, orthogonal deprotection strategies, heterocyclic library construction
Reactivity	Suitable for selective Boc deprotection (TFA/HCl), benzyl ester hydrogenolysis (Pd/C, H₂), ester transesterification, amide coupling (after deprotection), and sequential functionalization
Special Note	✅ Orthogonally Diprotected Scaffold—N-Boc (acid-labile) + benzyl ester (hydrogenolysis-labile) enable independent deprotection. Distinct from mono-protected analogs by synthetic flexibility. Part of our protected piperidine building block series.