Modular Access to N-Substituted cis 5-Amino-3-hydroxypiperidines

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Piperidine derivatives are crucial in drug discovery.
• Efficient synthesis of substituted piperidines is essential for medicinal chemistry.
• Accessing cis 5-amino-3-hydroxypiperidine scaffolds can be challenging.

Purpose of the Study:

• To develop a new synthetic strategy for N-substituted cis 5-amino-3-hydroxypiperidines.
• To provide a straightforward and versatile route to these important chemical structures.
• To enable access to drug-relevant scaffolds and fragments.

Main Methods:

• Utilized a sequence of oxidative cleavage, reductive amination, and reductive cleavage.
• Started from a readily available bicyclic adduct.
• Focused on efficient functionalization of the piperidine ring.

Main Results:

• Successfully prepared N-substituted cis 5-amino-3-hydroxypiperidines.
• Demonstrated the versatility of the developed synthetic route.
• Confirmed straightforward access to the target compounds.

Conclusions:

• The developed synthetic sequence provides efficient access to N-substituted cis 5-amino-3-hydroxypiperidines.
• This method represents a valuable tool for medicinal chemists seeking drug-relevant scaffolds.
• The straightforward nature of the route enhances its applicability in drug discovery programs.