A Concise Synthesis of Racemic Lorcaserin

作者：Xu, Bin; Su, Jincai; Wang, Jing^*; Zhou, Guo-Chun^*

来源：Australian Journal of Chemistry, 2016, 69(7): 770-774.

DOI：10.1071/CH15667

• CARBOXYLIC-ACIDS
• ACYCLIC IMIDES
• OBESITY
• DISCOVERY
• AGONIST

We report herein the concise synthesis of racemic lorcaserin (+/-)-1, which is an anti-obesity drug. The synthetic route involved the key synthesis of an asymmetrical imide intermediate 11 and its efficient reduction. Imide 11 was synthesized directly by the reaction of nitrile 9 with acid 10. The reducing system of NaBH4, AlCl3, and trimethylsilyl chloride efficiently fulfilled the reduction of imide 11 to amine 8a, which could be converted to (+/-)-1 via Friedel-Crafts reaction as reported. This route afforded 69% two-step yield of 8a from 9 via 11, and the concise synthesis of (+/-)-1 was completed in three steps. This route offers an alternative pathway to the synthesis of (+/-)-1 and its analogues.

• 出版日期2016
• 单位南京农业大学