Alkylation of N-boc-1,2,3,4-tetrahydroisoquinolines in the 1-position and its application to the synthesis of isoquinoline alkaloids |
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Authors: | Gary M. Coppola |
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Abstract: | Boc-protected 1,2,3,4-tetrahydroisoquinolines 2 can be lithiated with t-butyllithium in the presence of N,N,N',N',-tetramethylethylenediamine. Reaction of the anion with alkyl halides provides 1-alkyl N-Boc-1,2,3,4-tetrahydroisoquinolines in 67–71% yield. The protecting group is easily removed in high yield with trifluoroacetic acid. The alkaloids salsolidine ( 8 ) and laudanosine ( 11 ) were synthesized in racemic form using this method. |
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