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

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

1984-03-27

1987-01-27

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 44, C07D48908

Patent

active

046395202

ABSTRACT:
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.

REFERENCES:
patent: 2772270 (1956-11-01), Weiss
patent: 4472253 (1984-09-01), Schwartz
Schwartz & Wallace, "Efficient Synthesis of 14-Hydroxymorphinans from Codeine", J. Med. Chem. (1981), 24, pp. 1525-1528.
Hauser et al., "14-Hydroxycodeinone. An Improved Synthesis", J. Med. Chem. (1974), vol. 17, No. 10, p. 1117.
Iijima, Rice & Brossi, "The Oxidation of Thebaine with m-Chloroperbenzoic Acid", Helv. Chim. Acta (1977), vol. 60, Fasc. 7 Nr. 213, pp. 2135-2137.
Kirk & Wiles, "The Reaction of m-Chloroperbenzoic Acid with 3-Acetoxy-Steroidal 3,5-Dienes," Chem. Comm. (1970), p. 518.
Kirk & Wiles, "Competing Reactions in the Peroxyacid Oxidation of 3-Alkoxy-Steroidal 3,5-Dienes," Chem. Comm. (1970), pp. 1015-1016.
Bentley, The Chemistry of the Morphine Alkaloids, 1954, pp. 251, 252 & 262.

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