Dicyclohexylcarbodiimide → HCID 20638276, compound

Participants

Reaction Conditions

Reaction Steps

4,5α-Epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (2.64 g, 8 mmol) and 4-(4-methoxyphenyl)-butyric acid (1.55 g, 8 mmol) are dissolved in CH2Cl2 (30 ml) at 25° C. Then N,N'-dicyclohexylcarbodiimide (1.65 g, 8 mmol) and 4-dimethylaminopyridine (0.97 g, 8 mmol) are added to the stirred solution. After the solution has been stirred for a further 14 hours at 25° C. the precipitate is filtered oft and washed with CH2Cl2 (20 ml). The combined organic phase is washed with water (2×10 ml), dried (Na2SO4), filtered and concentrated in the Rotavapor. The residue thus obtained is purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1). The residue is freed from residual solvent under high vacuum in order to obtain 4,5α-epoxy-3-methoxymethoxy-6α-(4-(4-methoxyphenyl)-butyryloxy)-17-methyl-morphinan-7-ene (3.71 g, 91.7%)

Provenance & Evidence