tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

tert-Butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate (CAS 169206-65-9) is a strategically functionalized Boc-protected piperidine derivative engineered for pharmaceutical intermediate synthesis, ligand development, and heterocyclic 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 α,β-unsaturated methyl ester side chain at the C4 position (exocyclic double bond). The N-Boc protection prevents unwanted N-alkylation during synthetic sequences and can be removed under mild acidic conditions, while the conjugated ester moiety offers versatile reactivity including catalytic hydrogenation (to saturated methyl ester), Michael addition, or hydrolysis to the corresponding acid. Compared to its ethyl ester analog (CAS 135716-08-4), this methyl ester form offers slightly altered steric properties and hydrolysis kinetics, providing flexibility in synthetic route optimization. This intermediate is particularly valuable for constructing CNS-active pharmaceuticals, GPCR ligands, peptidomimetics, and piperidine-based scaffolds where controlled nitrogen reactivity and C4-functionalization are critical. Manufactured under controlled conditions, it supports drug discovery programs requiring modular access to differentially protected piperidine architectures with tunable side-chain reactivity.

Property

Product Name	tert-Butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate
CAS Number	169206-65-9
Chinese Name	叔丁基4-(2-甲氧基 -2-氧代亚乙基)哌啶-1-羧酸酯
Synonyms	Methyl (1-Boc-piperidin-4-ylidene)acetate; 1-Boc-4-(methoxycarbonylmethylene)piperidine; tert-Butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate
Chinese Synonyms	1-Boc-4-(甲氧羰基亚甲基) 哌啶; 甲基(1-Boc-哌啶-4-亚基)乙酸酯; Boc-哌啶不饱和甲酯; 4-(2-甲氧基-2-氧代亚乙基)哌啶-1-羧酸叔丁酯
Molecular Formula	C₁₃H₂₁NO₄
Molecular Weight	255.31 g/mol
Purity	≥ 98% (HPLC area normalization)
Product Category	Pharmaceutical Intermediates / Piperidine Derivatives / Protected Unsaturated Esters
Appearance	White to grayish-white solid
Boiling Point	~270-280°C at 760 mmHg (estimated)
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 strong oxidizing agents.
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, catalytic hydrogenation (to saturated methyl ester), Michael addition reactions, heterocyclic library synthesis
Reactivity	Suitable for selective Boc deprotection (TFA/HCl), ester hydrolysis (to acid), catalytic hydrogenation (to saturated methyl ester), Michael addition (conjugate addition), and sequential functionalization
Special Note	✅ Unsaturated Methyl Ester Scaffold—exocyclic double bond enables hydrogenation or Michael addition. Methyl ester vs. ethyl ester analog (CAS 135716-08-4) offers altered steric/hydrolysis properties. N-Boc enables orthogonal protection. Part of our protected piperidine building block series.