Journal of Heterocyclic Chemistry p. 1687 - 1691 (1995)
Update date:2022-08-04
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Klunder
Functionalization at the 3-position of the dipyridodiazepinone nevirapine (1) has been accomplished by Sommelet-Hauser rearrangement of an ylide derived from 1. Treatment of N-cyanomethylpyrrolidinium salt 4 with potassium tert-butoxide in a mixture of dimethylsulfoxide and tetrahydrofuran at -10°, followed by acid hydrolysis, afforded a mixture of compounds 5 and 6 in a ratio of 1:1.8. Upon treatment of 4 with sodium amide in liquid ammonia, 5 and 6 were obtained in a ratio of 1.5:1 and a combined yield of 83%. Compound 5 is the desired product resulting from Sommelet-Hauser rearrangement of 4, whereas 6 derives from competing Stevens rearrangement and intramolecular cyclization of the aldehyde produced upon hydrolysis. Baeyer-Villiger oxidation of 5 afforded the 3-hydroxy derivative 2, a recently identified metabolite of nevirapine.
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