Related Experiment Video
Updated: Jul 10, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Aminocarbonylation route to tolvaptan
Yasuhiro Torisawa1, Takuya Furuta, Takao Nishi
1Faculty of Pharmacy, Takasaki University of Health and Welfare, 60 Naka-Orui, Takasaki, Gunma 370-0033, Japan. torisawa@takasaki-u.ac.jp
A new palladium-catalyzed reaction efficiently synthesizes a key intermediate for tolvaptan, a drug used to treat hyponatremia. This one-step process improves the synthesis of this important pharmaceutical compound.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Catalysis
Background:
- Tolvaptan is a critical medication for treating hyponatremia.
- Efficient synthesis of tolvaptan intermediates is crucial for drug accessibility.
Purpose of the Study:
- To develop a streamlined synthetic route for a key tolvaptan intermediate.
- To explore palladium-catalyzed aminocarbonylation for this transformation.
Main Methods:
- Utilized palladium catalysis for aminocarbonylation.
- Employed aryl bromide and NH-benzazepinone as starting materials.
Main Results:
- Achieved effective synthesis of the target intermediate in a single step.
- Reported yields of the intermediate up to 85%.
Conclusions:
- The developed Pd-catalyzed aminocarbonylation is a highly efficient method for producing a key tolvaptan intermediate.
- This one-step synthesis offers a promising route for pharmaceutical production.
Related Concept Videos
Drug Metabolism: Phase II Reactions
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
Drug Excretion: Miscellaneous Routes
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Drug Elimination: Non-Renal Routes

