PREPARATION OF 14-HYDROXY-N-ETHOXY-CARBONYL-NORCODEINONE

摘要

N-ethoxycarbonyl-14-hydroxynorcodeinone is prepared by contacting N-ethoxycarbonyl-norcodeinone enol acetate with an aromatic or aliphatic mono-basic or poly-basic peroxy-acid under reaction conditions effective for substituting an -OH group in the 14-position of the norcodeinone enol acetate. In a preferred embodiment the reaction conditions include effecting the contacting in the presence of (A) a moderately strong acid having a pKa of from about 0.3 to about 3.5, (B) an inert organic solvent, and (C) in the substantial absence of water. Codeine is converted to noroxymorphone by an improved process employing the above method for introducing the 14-hydroxy group into the codeine derivative.