Methyl iodide → HCID 86600283, compound

Participants

Reaction Steps

A solution of 5β-benzyl-14β-butoxy-4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one (0.32 g, 0.72 mmol) and methyl iodide (0.51 g, 3.58 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 (0.41 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:6). Yield: 0.22 g (54%) slightly beige crystals of the compound 45. Fp. 188-195° C.; MS (CI): 462 (M+); IR (KBr): 1729 (C═O) cm−1; 1H-NMR (DMSO-d6, δ in ppm): 9.49 (s, OH), 7.28-7.20 (m, 5 arom. H), 6.69 (d, 1 arom. H, J=8.2 Hz), 6.62 (d, 1 arom. H, J=8.2 Hz), 3.61 (s, CH3N+, axial), 3.23 (s, CH3N+, equatorial), 1.01 (t, 3H, C14-O(CH2)3CH3, J=7.0 Hz).

Provenance & Evidence