An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization

A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation,...

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Main Authors:	Qi Liao, Lan Jiang, Cong Li, Yaling Shen, Min Wang, Chengkun Cao, Xiangnan Hu
Format:	Article
Language:	English
Published:	Hindawi Limited 2019-01-01
Series:	Journal of Chemistry
Online Access:	http://dx.doi.org/10.1155/2019/5375670

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spelling	doaj-f03a72335a9e475688b5e6adbce8a0392020-11-24T21:46:43ZengHindawi LimitedJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/53756705375670An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its OptimizationQi Liao0Lan Jiang1Cong Li2Yaling Shen3Min Wang4Chengkun Cao5Xiangnan Hu6Department of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaCollege of Environment and Resources, Chongqing Technology and Business University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaA mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.http://dx.doi.org/10.1155/2019/5375670
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu
spellingShingle	Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization Journal of Chemistry
author_facet	Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu
author_sort	Qi Liao
title	An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
title_short	An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
title_full	An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
title_fullStr	An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
title_full_unstemmed	An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
title_sort	efficient and practical method for the synthesis of saxagliptin intermediate 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid and its optimization
publisher	Hindawi Limited
series	Journal of Chemistry
issn	2090-9063 2090-9071
publishDate	2019-01-01
description	A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.
url	http://dx.doi.org/10.1155/2019/5375670
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An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization

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