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An asymmetric synthesis of (R)-5-(methylamino)-5,6-dihydro-4H-imidazo-[4,5,1-ij]quinolin-2(1H)-one (1) and its [2-14C]- and [6,7-3H2]-labeled forms

✍ Scribed by Richard F. Heier; Malcolm W. Moon; Wayne T. Stolle; John A. Easter; Richard S. P. Hsi

Publisher
John Wiley and Sons
Year
1996
Tongue
French
Weight
569 KB
Volume
38
Category
Article
ISSN
0022-2135

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✦ Synopsis

~R~

5,

quinolin-2( lm-one (1) is a dopamine agonist which shows selectivity for the D2 receptor subtype, and is of interest as a potential drug for the treatment of Parkinson's disease. An asymmetric epoxidation approach has been used to prepare 1 in eleven steps (15% overall yield) from 8-nitroquinoline. An advanced intermediate in this synthesis, tert-butyl (R.J-methyl@-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate (lo), has been reacted with ['4C]phosgene to provide a two-step synthesis of 1 labeled with carbon-14 at the C-2 position (236 pCi/mg). Bromination of 1 gave the dibromo analogue 12b which was reduced in the presence of tritium gas t o give 1 labeled with tritium at the C-6 and C-7 positions (28.5 Ci/mmol). In addition to providing syntheses for labeled forms of the drug which are useful in drug disposition and receptor binding studies, this approach also provides a convenient synthesis for the unlabeled form of drug.

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