1100748-68-2

Usage

Uses

Used in Pharmaceutical Industry:
1,9-Diazaspiro[5.5]undecane, 1-(phenylmethyl)is used as a building block for the synthesis of complex organic molecules, which can be further utilized in the development of new drugs and medical compounds. Its unique spiro structure and nitrogen atom in the center provide a foundation for the creation of diverse chemical entities with potential therapeutic applications.
Used in Organic Synthesis:
1,9-Diazaspiro[5.5]undecane, 1-(phenylmethyl)is used as a key intermediate in organic synthesis, allowing chemists to construct a wide range of complex organic molecules. Its spiro structure and functional groups enable the formation of various chemical bonds and reactions, facilitating the synthesis of target compounds with specific properties and applications.

Upstream product

• 1100748-67-1 C₂₁H₃₂N₂O₂ 

Relevant academic research and scientific papers

Synthesis of four novel natural product inspired scaffolds for drug discovery

Inspired by the novel spiro structures of a number of bioactive natural products such as the histrionicotoxins, a series of novel spiro scaffolds have been designed and robust syntheses developed. The scaffolds are ready-to-use building blocks and can be easily prepared on a 5-20 g scale. They contain two amino groups (one Boc-protected) and have been designed for ease of conversion to a lead generation library, using either amide formation or reductive amination procedures. The synthesis of the 1,9-diazaspiro[5.5]undecane and 3,7-diazaspiro[5.6]dodecane ring systems was achieved using RCM as the key step. A simple workup procedure is reported for the removal of highly colored ruthenium residues. The synthesis of the 1,8-diazaspiro[4.5]decane scaffold has been achieved using a bromine-mediated 5-endo cyclization of the corresponding 4-aminobutene intermediate under acidic conditions. This is the first example of this type of cyclization to be reported. A novel mechanism involving a bromine transfer reaction from an initially formed bromonium ion to a neighboring nitrogen atom is suggested as the reason for the failure of this type of reaction under "normal" bromination conditions. An unusual rearrangement of a 1-acyl-1,9-diazaspiro[5.5]undecane to the corresponding 9-acyl-1,9-diazaspiro[5.5]undecane is reported.