Allyl iodide → HCID 131727873, compound

Participants

Reaction Steps

A solution of 14-O-methyloxymorphone (Schmidhammer et al., J. Med. Chem. 1984, 27, pp. 1575-1579) (210 mg, 0.67 mmol) and allyl iodide (0.28 ml, 3.35 mmol) was stirred in 5 ml N,N-dimethylformamide for 7 days at 40° C. (bath temperature) and then evaporated down. The evaporation residue (484 mg of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH (250:5->250:12)). The evaporation residue (134 mg) was again purified using column chromatography (silica gel; CH2Cl2/MeOH (250:4.5)). Evaporation residue 77 mg (27%) of amorphous compound 43. Fp. >140° C.; IR (KBr): 1724 (CO) cm−1; 1H-NMR (DMSO-d6): δ 9.57 (s, C3-OH), 6.68 (s, 2 arom. H), 6.28-6.08 (m, 1 olef. H), 5.75-5.63 (m, 2 olef. H), 4.95 (s, C5-H), 3.42 (s, CH3O), 3.05 (s, +NCH3, equatorial); MS (CI): m/z 356 (M+).

Provenance & Evidence