A Facile Oxidation of Tertiary Amines to Lactams by Using Sodium Chlorite: Process Improvement by Precise pH Adjustment with CO2

Author:

Chu Changhu1,Liu Chaoyang1,Sun Haozhou1,Qin Cheng1,Yang Tiannuo1,Zhang Wenxian1,Zhou Yuan1,Li Yani1,Jia Zheng Robert2

Affiliation:

1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; Shanghai Key Laboratory of New Drug Design; School of Pharmacy, East China University of Science and Technology

2. Shanghai High School International Division

Abstract

AbstractBy using cheap and innocuous sodium chlorite, a series of tertiary amines have been oxidized to the corresponding lactams with good selectivity and high yield. In this method, neither transition-metal catalyst nor oxidant was used. In the oxidation step, the pH of the sodium chlorite was precisely adjusted to pH around 6 using CO2, such pH is a compromise between oxidative properties, chemical stability, and unwanted precipitation. In addition, buffer salts are not necessary, which allows this oxidation reaction to be performed under safe and environmentally benign conditions.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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