|14-Hydroxylated Codeine Analogues from Thebaine||Bookmark|
14-Hydroxylated Codeine Analogues
J Med Pharm Chem, Vol. 3, No. 3, pp 615-617 (1961)
14-Hydroxycodeinone was prepared from thebaine by the method of Feldman and Lyutenberg [*] was obtained in 85% yield, mp 268-269°C. A pure, white crystalline compound, mp 273-274°C [lit. m.p. 275-276°C], which was sensitive to light and air, could be obtained only after several recrystallizations from acetone and decolorizations with carbon.
14-Hydroxydihydrocodeinone was prepared by catalytic reduction of 14-hydroxycodeinone (2.50g, 0.008 moles) with PdCl2 (50 mg) in 10% acetic acid (85 ml) at over 800 mm hydrogen pressure. After 3 h, uptake of hydrogen was quantitative. The solution was filtered, made basic with ammonia, and extracted with chloroform. Evaporation of the solvent and recrystallization from absolute alcohol gave 2.13 g (0.0068 moles, 85%) of product, mp 220-221°C [lit. mp 219-221°C].
(*) Feldman & Lyutenberg, Zh. prikl. Khim., Leningr., 18, 715 (1945)