(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate: Key Facts & FAQs
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate: Key Facts & FAQs
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate is a chiral, enantiomerically enriched piperidine building block bearing a benzyloxycarbonyl (Cbz) protecting group at N-1 and an ethyl ester at C-3, widely used in asymmetric synthesis and as a pharmaceutical intermediate.
- SKU / Catalog Number
- B731874
- Chemical Name
- (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate
- Stereochemistry
- (S)-configuration at C-3 of the piperidine ring
- Key Functional Groups
- Cbz (benzyloxycarbonyl) carbamate at N-1; ethyl ester at C-3
- Primary Application
- Chiral building block for asymmetric synthesis and pharmaceutical intermediate preparation
- Supplier
- Aladdin Scientific
What Is (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate?
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate (Aladdin SKU B731874) is a chiral piperidine derivative in which the nitrogen is protected as a benzyl carbamate (Cbz group) and the C-3 position carries an ethyl ester with defined (S)-absolute configuration. The molecule belongs to the class of N-protected amino acid-type building blocks commonly employed in medicinal chemistry and total synthesis. The Cbz group can be removed selectively by catalytic hydrogenolysis, while the ethyl ester is amenable to saponification or further elaboration, making this compound a versatile synthetic intermediate.
Handling, Storage, and Safety
As with most chiral ester intermediates, (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate should be stored in a tightly sealed container away from moisture, heat, and light to preserve optical purity and chemical integrity. Standard laboratory precautions apply: use appropriate personal protective equipment (gloves, safety glasses, and lab coat) when handling the compound. Consult the product-specific Safety Data Sheet (SDS) available from Aladdin Scientific for full hazard classification, first-aid measures, and disposal guidance before use.
Note: Specific GHS hazard classifications for this SKU should be confirmed in the SDS; consult Aladdin Scientific customer support or the product page for the most current safety information.
Applications in Synthesis
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate serves as a key chiral building block in the synthesis of biologically active piperidine-containing natural products and drug candidates. The orthogonal protecting group strategy—Cbz on nitrogen, ethyl ester on carbon—allows sequential, selective deprotection and functionalization steps. Typical downstream transformations include: (1) Cbz removal via Pd/C-catalyzed hydrogenolysis to liberate the secondary amine for alkylation or acylation; (2) ester hydrolysis to give the free carboxylic acid for peptide coupling or decarboxylative modifications; and (3) reduction of the ester to the corresponding alcohol for further elaboration. Its well-defined (S)-stereocenter is critical for accessing enantiomerically pure target molecules in pharmaceutical research.
Ordering and Availability
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate is available from Aladdin Scientific under catalog number B731874. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and add the desired quantity to your cart. For bulk quantities, custom packaging, or certificate of analysis (CoA) requests, contact Aladdin Scientific's sales or customer service team directly. Lead times and available pack sizes may vary; please check the product page for real-time stock status and pricing information.
Frequently asked questions
What is the stereochemical configuration of (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate?
The compound possesses an (S)-absolute configuration at the C-3 position of the piperidine ring, as denoted by the (S) prefix in its IUPAC name. This defined stereocenter makes it a valuable enantiomerically enriched building block for asymmetric synthesis.
How should (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate be stored to maintain its integrity?
The compound should be stored in a tightly sealed container, protected from moisture, heat, and direct light. Refer to the Aladdin Scientific product page or SDS for the specific recommended storage temperature and any additional precautions applicable to this SKU.
What are the common synthetic applications of this compound?
(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate is primarily used as a chiral building block in pharmaceutical intermediate synthesis. Its orthogonal protecting groups—Cbz on nitrogen and an ethyl ester on C-3—allow selective deprotection and further functionalization to construct enantiomerically pure piperidine-containing target molecules.
How can the Cbz protecting group be removed from this compound?
The benzyloxycarbonyl (Cbz) group on the nitrogen can be selectively removed by catalytic hydrogenolysis, typically using palladium on carbon (Pd/C) as the catalyst under a hydrogen atmosphere. This releases the free secondary amine while leaving the ethyl ester intact under standard conditions.
Where can I find the Certificate of Analysis (CoA) or purity data for SKU B731874?
The Certificate of Analysis for (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate (SKU B731874) can be requested through the Aladdin Scientific website product page or by contacting Aladdin Scientific customer service directly. Lot-specific purity and analytical data are typically provided upon request.
References
- Aladdin Scientific product page for (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate, SKU B731874.
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience, 2007. (General reference for Cbz protection and deprotection strategies.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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