For organic chemists and process development scientists, understanding the reactivity and optimal use of key building blocks is essential for efficient synthesis. 1-Boc-piperidine-4-carboxaldehyde, identified by CAS number 137076-22-3, is a prime example of such a versatile intermediate, widely employed in pharmaceutical and fine chemical industries. This guide aims to illuminate its chemical properties, reactivity patterns, and applications, offering valuable insights for B2B professionals seeking to optimize their synthetic routes.

Chemical Profile of 1-Boc-piperidine-4-carboxaldehyde

1-Boc-piperidine-4-carboxaldehyde presents as a white crystalline powder, typically with a purity of 97% or greater. Its molecular formula is C11H19NO3, and its molecular weight is approximately 213.28 g/mol. The compound features a piperidine ring where the nitrogen atom is protected by a tert-butoxycarbonyl (Boc) group, and a formyl (aldehyde) group is attached at the 4-position of the ring. This structural arrangement provides distinct advantages in synthetic chemistry:

  • Boc Protection: The Boc group is a common and readily removable protecting group for amines. It renders the nitrogen atom less nucleophilic and basic, allowing selective reactions to occur at other parts of the molecule. It can be easily cleaved under acidic conditions (e.g., TFA, HCl) to reveal the free amine.
  • Aldehyde Reactivity: The formyl group is a highly reactive functional group. It readily undergoes nucleophilic addition reactions, such as Grignard reactions, Wittig reactions, and reductive aminations. It can also be oxidized to a carboxylic acid or reduced to an alcohol.

Optimizing Synthetic Strategies

The dual functionality of 1-Boc-piperidine-4-carboxaldehyde makes it a workhorse in constructing complex molecular architectures. Here are key strategies for its use:

  • Reductive Amination: Reacting the aldehyde with a primary or secondary amine in the presence of a reducing agent (e.g., sodium cyanoborohydride, sodium triacetoxyborohydride) is a powerful method to form new C-N bonds, extending carbon chains or building cyclic structures.
  • Carbonyl Additions: Using organometallic reagents like Grignard or organolithium reagents allows for the addition of alkyl, aryl, or vinyl groups to the carbonyl carbon, forming secondary alcohols. These alcohols can then be further manipulated.
  • Wittig Reaction: This reaction converts the aldehyde into an alkene, introducing unsaturation and allowing for further functionalization or chain extension.
  • Deprotection and Further Functionalization: After performing desired reactions at the aldehyde site, the Boc group can be removed to unmask the piperidine nitrogen, which can then be subjected to N-alkylation, N-acylation, or other amine-specific reactions.

Applications in Pharmaceutical Synthesis

The utility of 1-Boc-piperidine-4-carboxaldehyde is extensively documented in the synthesis of various APIs and lead compounds, including:

  • Pim-1 kinase inhibitors
  • Selective GPR119 agonists (for type II diabetes)
  • M-tropic (R5) HIV-1 replication inhibitors
  • HDAC inhibitors
  • Selective 5-HT6 antagonists

Sourcing and Supplier Considerations

For B2B clients, sourcing high-quality 1-Boc-piperidine-4-carboxaldehyde (CAS 137076-22-3) from reliable manufacturers is crucial for consistent synthetic outcomes. When selecting a supplier, prioritize those offering detailed product specifications, Certificates of Analysis (CoA), and competitive pricing. Companies specializing in fine chemicals and pharmaceutical intermediates, particularly those based in China, are often well-equipped to meet these demands. Ensure the supplier can provide the required purity (97% min) and offers appropriate packaging and timely delivery to support your research and manufacturing schedules.

Conclusion: A Cornerstone for Synthetic Chemists

1-Boc-piperidine-4-carboxaldehyde remains a cornerstone for many complex synthetic endeavors in the pharmaceutical industry. By understanding its chemical properties and reactivity, and by partnering with dependable suppliers, B2B customers can effectively leverage this intermediate to drive innovation and achieve their synthesis goals. We are dedicated to providing high-quality chemical building blocks to support your scientific and manufacturing needs.