Methyl iodide → HCID 86600280, compound

Participants

Reaction Steps

A solution of 4,5α-epoxy-3-hydroxy-17-methyl-14β-[(3-phenylpropyl)oxy]morphinan-6-one (oil, 257 mg, 0.61 mmol) and methyl iodide (0.38 ml, 6.11 mmol) in acetonitrile (10 ml) was stirred for 2 days at 50° C. (bath temperature) under N2. A DC examination showed that the reaction was not concluded. Therefore further methyl iodide (0.38 ml, 6.11 mmol) was added and the solution stirred further for 3 days under the same conditions. Then the solvent was evaporated off and the evaporation residue (367 mg of yellow foamy resin) was purified using column chromatography (silica gel; CH2Cl2/MeOH (10:1)). Evaporation residue 240 mg (71%) amorphous compound 38. Fp. 164-170° C.; IR (KBr): 1723 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.57 (s, C3-OH), 7.3-7.16 (m, 5 arom. H), 6.67 (s, 2 arom. H, C1—H, C2—H), 4.88 (s, C5—H), 3.56 (s, N+CH3, axial), 3.21 (s, +NCH3, equatorial); MS (CI): m/z 434 (M+).

Provenance & Evidence