A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2- oxoacetic acid and it's optimization. | [Pakistan Journal of Pharmaceutical Sciences • 2018]

Author(s):

1. Hui-fei Wang: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

2. Run Gan: Bishan Area Maternal and child health care Hospital. Bishan,Chongqing,PR China

3. Jing Zhou: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

4. Qi Liao: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

5. Tian-bao Wang: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

6. Cai-ling Zhong: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

7. Yuan-yuan Xiang: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

8. Hong-bo Lin: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

9. Xiang-nan Hu: Department of Pharmacy, Chongqing Medical University,Chongqing,PR China

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%.

Page(s): 1393-1397

DOI: DOI not available

Published: Journal: Pakistan Journal of Pharmaceutical Sciences, Volume: 31, Issue: 4, Year: 2018

Keywords:

onepot method

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