Methyl iodide → HCID 86600287, compound

Participants

Reaction Steps

A solution of 14β-[(4-chlorobenzyl)oxy]-17-cyclopropylmethyl-4,5α-epoxy-3-hydroxymorphinan-6-one (0.50 g, 1.07 mmol) and methyl iodide (0.76 g, 5.37 mmol) in 8 ml of water-free acetonitrile was stirred under N2 at 40° C. (bath temperature) for 6 days and then evaporated down. The residue (0.56 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:4). Yield: 0.07 g (11%) of beige crystals of the compound 51. Fp. 214-219° C.; MS (CI): 480 (M+); IR (KBr): 1733 (C═O) cm−1; 1H-NMR (DMSO-d6 δ in ppm): 9.57 (s, OH), 7.57 (d, 2 arom. H, C14-OCH2Ph—Cl, J=8.6 Hz), 7.48 (d, 2 arom. H, C14-OCH2Ph—Cl, J=8.6 Hz), 6.71 (s, 2 arom. H), 5.10 (s, CH-5), 4.86 (d, 1H, C14-OCH2, J=11.4 Hz), 4.75-4.66 (m, 3H, C14-OCH2 and CH-9), 3.44 (s, CH3N+, axial).

Provenance & Evidence