tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate

tert-Butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate is a high‑purity, pharma‑grade intermediate supplied by Cosperpharm for the development and manufacturing of non‑β‑lactam β‑lactamase inhibitors. This compound serves as a key precursor to the diazabicyclooctane core found in avibactam and relebactam – antibiotic adjuvants that restore the activity of β‑lactam antibiotics against resistant Gram‑negative pathogens. Because tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate retains the exact (2S,5R) chirality required for target enzyme inhibition, it enables efficient, stereocontrolled assembly of the final API. Moreover, tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate is also used as an analytical reference standard (avibactam impurity 115) for quality control and impurity profiling. At Cosperpharm, each batch of tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate is manufactured under strict GMP‑aligned protocols and supplied with full documentation to support your process development and regulatory filings.

Product Parameters

Why Cosperpharm?

Cosperpharm combines technical expertise with a streamlined supply chain to deliver high‑quality intermediates and reference standards. Our GMP‑inspired facilities and in‑house analytical lab (HPLC, LC‑MS, NMR, GC) ensure that every shipment meets or exceeds your purity specifications. We offer transparent documentation – including COA, stability data, and impurity profiles – to simplify your regulatory submissions. With a dedicated customer support team and competitive lead times, Cosperpharm has become a trusted partner for over 30 global pharmaceutical companies. For tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate, we maintain safety stock and can scale from R&D grams to commercial kilograms efficiently.

Product Advantages

1.Exact (2S,5R) chirality – Verified by chiral HPLC; the correct stereochemistry is essential for the β‑lactamase inhibitory activity of final APIs such as avibactam and relebactam.

2.Orthogonal protecting groups – The Boc group (cleavable under mild acid) and the benzyloxyamino group (cleavable by hydrogenolysis) allow stepwise unmasking without cross‑reactivity.

3.Stable carboxamide linkage – Provides robust connectivity between the two piperidine rings, resisting hydrolysis during multi‑step synthesis.

4.High crystalline purity – Isolated as a solid, easy to handle and weigh, with ≥98% HPLC purity.

5.Versatile reactivity – The free secondary amine (after Boc removal) and the hydroxylamine (after debenzylation) can be used for cyclization to form the diazabicyclooctane scaffold.

Synthetic Route

The synthesis of tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate follows a chiral pool approach starting from L‑pyroglutamic acid. After establishing the (2S,5R) piperidine core, the 5‑benzyloxyamino group is introduced via stereoselective amination or oximation/reduction. The piperidine‑2‑carboxylic acid intermediate is then activated and coupled with N‑Boc‑piperidin‑4‑amine using a standard coupling reagent such as HOBt/EDC. A representative procedure from CN111606844 reports the reaction of the acid intermediate with the amine in the presence of AlCl₃ in toluene at 50 °C for 3 h, followed by aqueous work‑up and crystallization from petroleum ether, achieving 88% yield. The product is often isolated as the tosylate salt to improve crystallinity. Cosperpharm can provide non‑confidential process details under a mutual agreement.

Contact Us

Ready to order tert-butyl 4-((2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylate? Request a sample, quote, or technical consultation from Cosperpharm today.