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Remarkable effect of water in a regioselective lithiation of 5-(tert-butoxycarbonyl)-7-methoxy-1-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline

✍ Scribed by Yoshihiro Moro-oka; Satoru Iwakiri; Tsutomu Fukuda; Masatomo Iwao

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
180 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

5-(tert-Butoxycarbonyl)-7-methoxy-1-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline (1b) was lithiated regioselectively at C-6 with sec-BuLi (3.0 equiv.) in the presence of water (1.0 equiv.) in ether at ^78 C. Under conventional conditions, 1b was lithiated non-regioselectively at the C-6, C-8 and C-2 positions.

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