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Note | Special issue | Vol 82, No. 1, 2010, pp.887-893
Published online, 29th July, 2010
DOI: 10.3987/COM-10-S(E)50
Convenient Synthesis of Optically Pure 8-Methoxy-2-methyl-1,2,3,4-tetrahydroquinoline and 2-Methyl-1,2,3,4-tetrahydroquinoline

Jie Tang, Guo-Fang Jiang,* and Yong-Gui Zhou*

*Dalian Institute of Chemical Physics, 457 Zhongshan Road, Dalian 116023, China

Abstract

A convenient method was developed to synthesize optically pure 8-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline (2a) and 2-methyl-1,2,3,4-tetra-hydroquinoline (2b) by combining the methods of catalytic hydrogenation and classical resolution. The catalytic system ([Ru(p-cymene)Cl2]2/I2) showed high efficiency in preparing racemic 2a and 2b, which were successfully resolved using commercial tartaric acid derivatives, and both enantiomers were obtained in moderate yield with >99% ee.