Chemical Identity and Structure

(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate (Aladdin SKU B731874) is a six-membered nitrogen heterocycle bearing two distinct ester functionalities: a benzyloxycarbonyl (Cbz) carbamate on the ring nitrogen and an ethyl ester at the 3-position carbon, which carries the (S) stereocenter. The Cbz group serves as a standard, hydrogenolytically removable nitrogen-protecting group, while the ethyl ester can be selectively saponified or reduced under controlled conditions. The orthogonal deprotection profile of these two groups makes this compound particularly valuable as a bifunctional chiral scaffold. The piperidine ring confers conformational rigidity relative to acyclic analogs, which can translate into improved stereoselectivity in downstream transformations. The molecular formula is C₁₆H₂₁NO₄ with a molecular weight of approximately 307.35 g/mol.

Handling, Storage, and Safety Guidelines

Storage: Store (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate under an inert atmosphere (nitrogen or argon) at 2–8 °C in a tightly sealed container, protected from moisture and direct light. Prolonged exposure to air, heat, or moisture may lead to hydrolysis of the ester or carbamate functionalities, compromising stereochemical integrity and purity.

Handling: Use standard laboratory personal protective equipment including nitrile gloves, safety spectacles, and a laboratory coat. Weigh and transfer the compound in a well-ventilated fume hood. Minimize exposure to air during transfer by working under a stream of inert gas when possible. Avoid contact with strong acids, strong bases, and oxidizing agents, as these may degrade the protecting groups or the chiral center.

Disposal: Dispose of waste material in accordance with applicable local and institutional regulations for organic chemical waste. Do not pour into drains or water supplies. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for jurisdiction-specific disposal requirements.

Note: A complete SDS for B731874 is available from Aladdin Scientific upon request or via the product page.

Applications in Asymmetric Synthesis

(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate serves as a versatile chiral synthon for the enantioselective construction of piperidine-containing target molecules. Its principal applications include:

• Pharmaceutical intermediate synthesis: The compound is a direct precursor to enantiomerically enriched piperidine derivatives found in a range of biologically active compounds. The defined (S)-stereocenter allows for the reliable transfer of chirality to downstream products without requiring additional chiral resolution steps.
• Selective deprotection strategies: The orthogonal combination of a Cbz group (removed by hydrogenolysis, e.g., H₂/Pd-C) and an ethyl ester (cleaved by saponification with aqueous base or LiOH) allows synthetic chemists to unmask either functional group independently, facilitating divergent synthesis from a single scaffold.
• N-functionalization: After Cbz removal, the free amine can be acylated, alkylated, or coupled to form amides, expanding the structural diversity accessible from this building block.
• Ester elaboration: The ethyl ester at C-3 can be reduced to the alcohol (e.g., LiAlH₄ or DIBAL-H), converted to the carboxylic acid, or used in Claisen condensation-type reactions to introduce additional carbon frameworks adjacent to the stereocenter.

Researchers should verify the enantiomeric excess (ee) of the received batch using chiral HPLC or optical rotation measurements before use in stereoselective sequences.

Quality, Purity, and Analytical Verification

Aladdin Scientific supplies (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate (B731874) as a research-grade reagent. Users are advised to perform the following analytical checks upon receipt and before critical synthetic use:

• Identity confirmation: ¹H NMR and ¹³C NMR spectroscopy in CDCl₃ or DMSO-d₆ to confirm the piperidine ring proton pattern, Cbz benzyl signals (δ ~5.1 ppm, CH₂; δ ~7.3 ppm, ArH), and ethyl ester signals (δ ~1.2 ppm, CH₃; δ ~4.1 ppm, OCH₂). Rotamers arising from restricted rotation about the Cbz carbamate bond may produce doubled NMR signals; this is a known phenomenon for N-Cbz piperidines and does not indicate impurity.
• Purity assessment: Reverse-phase HPLC (C18 column, UV detection at 210 or 254 nm) or GC analysis to confirm chromatographic purity consistent with the certificate of analysis (CoA).
• Stereochemical verification: Chiral HPLC (e.g., Chiralpak IA/IB/AD column) or optical rotation measurement in an appropriate solvent to confirm enantiomeric excess ≥98% ee (verify against the CoA specification for each lot).
• Moisture content: Karl Fischer titration if moisture-sensitive downstream reactions are planned.

Contact Aladdin Scientific's technical support team to obtain the Certificate of Analysis and Safety Data Sheet for the specific lot number of B731874.

Ordering, Specifications, and Grade Information

(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate is available from Aladdin Scientific under SKU B731874. Please refer to the current product page or contact your regional Aladdin Scientific representative for up-to-date information on:

• Available pack sizes and pricing
• Current stock availability and lead times
• Purity grade specifications and lot-specific CoA
• Bulk or custom quantity inquiries

When ordering, confirm the exact CAS number and (S)-stereodescriptor to ensure you receive the correct enantiomer, as both (R)- and racemic forms may be available from various suppliers. Aladdin Scientific's procurement team can assist with institutional purchase orders, custom quotations, and expedited shipping arrangements. For questions regarding reagent specifications, grade suitability, or technical compatibility with your synthetic workflow, contact technical support via the Aladdin Scientific website.