Stereoselective Synthesis of Endo-N-Boc Nortropine
FANG Yuan-ying1, WANG Qi1, LI Zhi-feng1, JIN Yi1, XU Jun2, YANG Zun-hua2
1. National Engineering Research Center for Manufacturing Technology of TCM Solid Preparation, Jiangxi University of Traditional Chinese Medicine, Nanchang 330006, China; 2. College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China
Abstract：Demethylated tropinone(1) was synthesized by reaction of tropinone with 1-chloroethyl chloroformate. N-Boc nortropinone(2) was prepared by reaction of 1 with Boc anhydride. 2 was reduced by lithium tri-sec-butylborohydride to achieve endo-N-Boc nortropine stereoselectively(endo/exo=6.5/1) with an overall yield of 60%. The structure was confirmed by 1H NMR and ESI-MS.
2015, Vol. 23 
