Methyl iodide → HCID 86600286, compound

Participants

Reaction Steps

A solution of 14β-butoxy-4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one (0.53 g, 1.49 mmol) and methyl iodide (1.06 g, 7.44 mmol) in 10 ml of water-free acetonitrile was stirred under N2 at 40° C. (bath temperature) for 2 days and then evaporated down. The evaporation residue (0.70 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:4). Yield: 0.31 g (42%) of colourless crystals of the compound 47. Fp. 180-185° C.; MS (CI): 372.2 (M+); IR (KBr): 1726 (C═O) cm−1; 1H-NMR (DMSO-d6, δ in ppm): 9.55 (s, OH), 6.68 (s, 2 arom. H), 4.95 (s, CH-5), 3.57 (s, CH3N+, axial), 3.21 (s, CH3N+, equatorial), 0.94 (t, O(CH2)3CH3, J=7.3 Hz).

Provenance & Evidence