Related Experiment Video
Updated: Nov 19, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Enantiomeric Separation and Thermodynamic Investigation of (R)-N-Tert-Butoxy Carbonyl-Piperidine-3-Carboxylic Acid
Vipul P Rane1, Vinod K Ahirrao1, Kiran B More1
1Wockhardt Research Centre, D-4, MIDC, Chikalthana, Aurangabad 431006, India.
Abstract:
A new selective, accurate and precise chiral high-performance liquid chromatography method for the separation of (R)-N-tert-butoxy carbonyl-piperidine-3-carboxylic acid hydrazide (RE) and its enantiomer was developed. RE is a key starting material of novel β-lactam enhancer drug Zidebactam. Chiral resolution of more than 10 was achieved on Chiralpak IA column using mobile phase consisting of n-hexane, ethanol in the ratio of 70:30, v/v. The flow rate of the mobile phase was 1.0 mL min-1 and the column oven temperature was 30°C. Detection was carried out at 225 nm. The developed method was validated as per the International Conference on Harmonization guideline. Limit of detection and limit of quantification of the enantiomeric impurity (S)-N-tert-butoxy carbonyl-piperidine-3-carboxylic acid hydrazide (SE) was 2.5 and 7.5 μg mL-1, respectively. Mean recovery of the SE was 96.83 ± 1.4%. The effect of thermodynamic parameters on the chiral separation was evaluated.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Prochirality
E2 Reaction: Stereochemistry and Regiochemistry
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
E1 Reaction: Stereochemistry and Regiochemistry
Racemic Mixtures and the Resolution of Enantiomers
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

