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Communication | Regular issue | Vol 32, No. 9, 1991, pp.1699-1703
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5798
Preparation of Tetrahydroisoquinolines from N-(tert-Butoxycarbonyl)-2-methylbenzylamines

Robin D. Clark* and Jahangir

*Institute of Organic Chemistry, Syntex Research, Palo Alto, California 94304, U.S.A.


Dilithiation of N-(tert-butoxycarbonyl)-2-methylbenzylamine (1a) followed by treatment with N,N-dimethylformamide affords 2-(tert-butoxycarbonyl)-3-hydroxytetrahydroisoquinoline (3a). Dehydration and reduction of 3a afford BOC-tetrahydroisoquinoline (5a). The methodology is also applicable to synthesis of chloro and fluoro substituted tetrahydroisoquinolines (5b,c), 3 and 4 substituted derivatives (8, 10), and the hexahydro-2H-benzoquinolizine ring system (13).