Dicyclohexylcarbodiimide → HCID 15384845, compound

Participants

Reaction Conditions

Reaction Steps

4,5α-Epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (1.98 g, 6 mmol) and thiophene-2-acetic acid (0.853 g, 6 mmol) are dissolved in CH2Cl2 (30 ml) at 25° C. Then N,N'-dicyclohexylcarbodiimide (1.24 g, 6 mmol) and 4-dimethylaminopyridine (0.73 g, 6 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 off and washed with CH2Cl2 (20 ml). The combined organic phase is washed with water (2×10 ml), dried (Na2SO4), filtered and evaporated down using a Rotavapor. The residue thus formed is purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1). The residue is freed from residual solvent in a high vacuum in order to obtain 4,5α-epoxy-3-methoxymethoxy-17-methyl-6α-((2-thienyl)-acetyloxy)-morphinan-7-ene (2.07 g, 76.1%) as a colourless foam.

Provenance & Evidence