(R)-N-Boc-3-aminomethylpiperidine

Synthesis

Using 3-piperidineacetic acid as a starting material, the important pharmaceutical intermediate 1-Boc-3-aminomethylpiperidine was synthesized in a five-step reaction involving esterification, reduction, tert-butyloxycarbonyl protection, bromination, and methylamination, with an overall yield of 72%. (R)-N-Boc-3-aminomethylpiperidine was then prepared by chiral resolution. The synthetic route is shown below:

Figure 1 Synthetic route of (R)-N-Boc-3-aminomethylpiperidine

Uses

(R)-1-Boc-3-aminomethylpiperidine is an important intermediate in the synthesis of many drugs. A series of checkpoint kinase 1 (CHK1) inhibitors have been synthesized using (R)-1-Boc-3-aminomethylpiperidine as a starting material, showing some efficacy in treating rheumatoid arthritis. A series of drugs for treating diseases related to MCH (melanin-concentrating hormone) have also been synthesized using this compound, showing some effectiveness in treating metabolic disorders. G-protein-coupled receptor (GPCR) agonists containing the 1-N-Boc-4-methylaminomethylpiperidine structural unit have been synthesized, which can be used to treat obesity and diabetes. A series of drugs for regulating metabolism and treating cardiovascular diseases have also been synthesized using (R)-1-Boc-3-aminomethylpiperidine.