Phenethyl bromide → HCID 10874002, compound

Participants

Reaction Steps

A mixture of 4,5α-epoxy-14-ethoxy-3-methoxy-5-methylmorphinan-6-one hydrochloride (H. Schmidhammer et al., Helv. Chim. Acta Vol. 76, 476-480,1993) (3.0 g, 7.88 mmol), potassium carbonate (3.9 g, 28.2 mmol), 2-phenylethyl bromide (1.41 ml, 10.4 mmol), and of 20 ml anhydrous NN-dimethyl formamide was stirred at 80° C. (bath temperature) for 2h. After cooling and addition of 130 ml of H2O, the mixture was extracted with diethyl ether (3×60 ml). The combined organic layers were washed with H2O(3×70 ml), dried over Na2SO4 and evaporated. The residue (3.6 yellow oil) was crystallized from MeOH to afford 2.1 g (70%) of 4,5α-epoxy-14-ethoxy-3-methoxy-5-methyl-17-(2-phenyl)ethylmorphinan-6-one (compound 3). M.p. 86-89° C. IR (KBr): 1725 (CO) cm-1. CI-MS: m/z 448 (M+ +1). 1H-NMR (CDCl3): δ 7.21 (m, 5 arom. H), 6.64 (d,J=8.2 Hz, 1 arom. H, 6.54 (d, J=8.2 Hz, 1 arom. H.), 3.85 (s, OCH3), 1.60 (s, CH3 --C(5)), 1.12 (t, J=6.8 Hz, CH3). Analysis calculated for C28H33NO4 (447.55): C 75.14, H 7.43, N 3.13; found: C 75.04, H 7.69, N 3.26.

Provenance & Evidence