Mallinckrodt, Inc.

Mallinckrodt Medical, Inc.

Imc Chemical Group, Inc.

Frank Kavka

Donald E Robertson

Wilbert Herbert Urry

Preparation of nalbuphine having low levels of .beta.-epimer

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 pK.sub.a 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.

Preparation of 14-hydroxy-N-ethoxy-carbonyl-norcodeinone

A method is disclosed for preparing dideoxyzearalane and related compounds which comprises reacting a hexahydrozearalin with an organic sulfonyl chloride to form a sulfonate ester derivative; recovering the sulfonate ester derivative; and catalytically dehydrosulfonyloxylating and aromatizing the sulfonate ester derivative to form the desired product.

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St. Louis, MO, United States of America

Frank Kavka