A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid and it's optimization.

Abstract

2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid (IV), a key intermediate of saxagliptin for type 2 diabetes mellitus (T2DM), was prepared from 1-adamantanecarboxylic acid(I) via oxidation by potassium permanganate(KMnO4) to afford 3-hydroxy-1-adamantanecarboxylic acid (II), which was treated with a one-pot method to give 1-acetyl-3-hydroxyadamantane (III) followed by oxidation. Some key steps were optimized and the overall yield was about 51%.

• Authors: Hui-Fei Wang, Run Gan, Jing Zhou, Qi Liao, Tian-Bao Wang, Cai-Ling Zhong, Yuan-Yuan Xiang, Hong-Bo Lin, Xiang-Nan Hu
• Journal: Pakistan journal of pharmaceutical sciences (Pak J Pharm Sci) Vol. 31 Issue 4 Pg. 1393-1397 (Jul 2018) ISSN: 1011-601X [Print] Pakistan
• PMID: 30033425 (Publication Type: Journal Article)

Chemical References

• Acetates
• Dipeptides
• Hypoglycemic Agents
• Potassium Permanganate
• adamantanecarboxylic acid
• saxagliptin
• Adamantane

Topics

• Acetates (chemical synthesis, chemistry, pharmacology)
• Adamantane (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• Chemistry Techniques, Synthetic (methods)
• Dipeptides (chemistry)
• Hypoglycemic Agents (chemical synthesis, chemistry, pharmacology)
• Molecular Structure
• Potassium Permanganate (chemistry)