Tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

Tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (CAS 135716-09-5) is a versatile piperidine derivative with a molecular weight of 271.35 g/mol and a standard purity of ≥98%. This compound is widely recognized as a PROTAC linker — a structural component that connects the E3 ubiquitin ligase ligand and the target protein ligand in proteolysis‑targeting chimera molecules — and can be used to synthesize PROTAC molecules for targeted protein degradation.

In modern drug development, tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate serves as a key intermediate in the synthesis of the poly(ADP-ribose) polymerase (PARP) inhibitor niraparib (brand name ZEJULA), which is FDA-approved for the treatment of epithelial ovarian, fallopian tube, and primary peritoneal cancer. PARP inhibitors work by blocking enzymes responsible for DNA repair, leading to selective cell death in cancer cells with defective DNA repair mechanisms. Certain derivatives of tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate have also demonstrated moderate antibacterial and antifungal activities, highlighting their potential in antimicrobial agent development.

In addition, tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate and its derivatives have been thoroughly characterized using FT‑IR, NMR, LCMS, and single‑crystal X‑ray diffraction, with detailed intermolecular interactions and crystal packing analyzed via Hirshfeld surface studies.

Product Parameters

Synthetic Routes

Using tert-butyl 4-(2-ethoxy-2-oxoethylene)piperidine-1-carboxylate (22 g, 81.8 mmol) as the starting material, the mixture was added to wet 10% Pd/C (2.2 g) and ethanol (160 mL). The mixture was degassed and backfilled with hydrogen three times. Under hydrogen chemical balloon protection, the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the catalyst was filtered off, and the filtrate was concentrated to yield tert-butyl 4-(2-ethoxy-2-oxyethyl)piperidine-1-carboxylate (22.5 g, yield 100%). LRMS analysis confirmed a m/z value of 172.1 (M-100), matching the theoretical value of 172.1.

Product Advantages

1.PROTAC linker utility – tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate is a recognized PROTAC linker that connects E3 ubiquitin ligase ligands to target protein ligands, enabling selective degradation of disease-causing proteins via the ubiquitin-proteasome system.

2.Key intermediate for niraparib synthesis – This compound serves as an essential building block in the synthesis of the FDA-approved PARP inhibitor niraparib (ZEJULA) for ovarian and breast cancer treatment.

3.Orthogonal functional groups – The Boc-protected amine (acid-labile) and ethyl ester (base- or nucleophile-labile) enable orthogonal deprotection strategies, allowing sequential modifications in multi-step syntheses

4.Antimicrobial potential – Certain derivatives of tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate have demonstrated moderate antibacterial and antifungal activities, suggesting potential as antimicrobial agents.

5.Comprehensive characterization – The compound has been extensively characterized by FT‑IR, NMR, LCMS, and single‑crystal X‑ray diffraction, with detailed crystallographic analysis available.

6.High purity – Standard ≥98% (HPLC/GC) ensures reliable and reproducible results; higher purity grades available upon request.

7. Versatile reaction chemistry – Capable of undergoing oxidation (to ketones or carboxylic acids) and reduction (to alcohols or amines) under controlled conditions.

Frequently Asked Questions (FAQ)

Q1: What are the primary applications of tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate?

A: This compound is primarily used as a PROTAC linker for synthesizing PROTAC molecules in targeted protein degradation research, and as a key intermediate in the synthesis of the PARP inhibitor niraparib for cancer therapy.

Q2: What is a PROTAC linker?

A: A PROTAC linker connects an E3 ubiquitin ligase ligand to a target protein ligand, allowing the PROTAC molecule to bring the target protein into proximity with the ubiquitin-proteasome system for selective degradation.

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