Methyl iodide → 17(R)-4,5alpha-epoxy-3-hydroxy-14beta-methoxy-17-methyl-6-oxo-17-(2-phenylethyl)morphinanium-iodide

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Reaction Steps

A solution of 4,5α-epoxy-3-hydroxy-14β-methoxy-17-(2-phenylethyl)morphinan-6-one (0.32 g, 0.7 mmol) and methyl iodide (0.56 g, 3.92 mmol) in 6 ml of water-free acetonitrile was stirred under N2 40° C. (bath temperature) for 2 days and then evaporated down. The residue (0.32 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:2). Yield: 0.07 g (16%) of colourless crystals of the compound 52. Fp. 180-181° C.; MS (CI): 420 (M++1); IR (KBr): 1727 (C═O) cm−1; 1H-NMR (D2O, δ in ppm): 7.17-7.14 (m, 5 arom. H), 6.56 (s, 2 arom. H), 5.18 (s, CH-5), 3.64 (s, CH3N+, axial), 3.44 (s, OCH3).

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