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HOME >> API >> API List 4 >> Noroxymorphone >> Patient Information

Noroxymorphone CAS No.: 33522-95-1

CAS No.: 33522-95-1

Parent Case Data:

This application is a continuation-in-part of application Ser. No. 196,539, filed Jul. 18, 1988, now agandoned, which was a continuation of application Ser. No. 863,209, filed May 14, 1986, now abandoend, which was a continuation of application Ser. No. 713,932, filed Mar. 20, 1985, now abandoned, which was a continuation-in-part of application Ser. No. 593,744, filed Mar. 27, 1984, now abandoned, which is incorporated herein by reference.
What is claimed is:

1. A process for preparing noroxymorphone from morphine comprising:

(1) reacting morphine in a single step with a haloformate ester of the formula X--C(O)OR1, wherein X is halogen and R1 is alkyl, so as to form 3,17-(di-R1 -oxycarbonyl)normorphine;

(2) oxidizing the hydroxyl group of the 3,17-(di-R1 -oxycarbonyl)normophine with an oxidizing agent, under acidic conditions at a pH of less than 1.0, so as to form 3,17-(di-R1 -oxycarbonyl)normorphinone;

(3) acylating the 3,17-(di-R1 -oxycarbonyl) normophinone with an acylating agent so as to form 3,17-(di-R1 -oxycarbonyl)normorphinone dienol acylate;

(4) contacting the dienol acylate with a peroxy oxidation agent so as to introduce a beta-oriented hydroxyl group in position 14 of said dienol acylate, so as to form 14-hydroxy 3,17-(di-R1 -oxycarbonyl)normorphinone;

(5) hydrogenating the 14-hydroxy-3,17-(di-R1 -oxycarbonyl)normorphinone in a reduction reaction so as to form 3,17-(di-R1 -oxycarbonyl)noroxymorphinone; and

(6) hydrolysing the 3,17-(di-R1 -oxycarbonyl) noroxymorphinone under hydrolytic conditions, so as to form noroxymorphone.

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