Barr Laboratories, Inc.

David Wayne Ray, Jr

Yousry Abdelrehim Sayed

Shaileshkumar Ramanlal Desai

The present invention relates to a process for the synthesis of oxandrolone from mestanolone. The process comprises the steps of: (a) oxidizing mestanolone to form 17&#x3b2;-hydroxy-17&#x3b1;-methyl-5&#x3b1;-androst-1-en-3-one; (b) hydroxylating the 17&#x3b2;-hydroxy-17&#x3b1;-methyl-5&#x3b1;-androst-1-en-3-one to form 1&#x3b1;, 2&#x3b1;, 17&#x3b2;-trihydroxy-17&#x3b1;-methylandrostan-3-one; (c) cleaving the 1&#x3b1;, 2&#x3b1;, 17&#x3b2;-trihydroxy-17&#x3b1;-methylandrostan-3-one to form 17&#x3b2;-hydroxy-17&#x3b1;-methyl-1-oxo-1,2,-seco-A-nor-5&#x3b1;-androstan-2-oic acid; and (d) reducing the 17&#x3b2;-hydroxy-17&#x3b1;-methyl-1-oxo-1,2,-seco-A-nor-5&#x3b1;-androstan-2-oic acid to form oxandrolone.

Process for the production of oxandrolone

The present invention relates to a process for the synthesis of oxandrolone from mestanolone. The process comprises the steps of: (a) oxidizing mestanolone to form 17&bgr;-hydroxy-17&agr;-methyl-5&agr;-androst-1-en-3-one; (b) hydroxylating the 17&bgr;-hydroxy-17&agr;-methyl-5&agr;-androst-1-en-3-one to form 1&agr;, 2&agr;, 17&bgr;-trihydroxy-17&agr;-methylandrostan-3-one; (c) cleaving the 1&agr;, 2&agr;, 17&bgr;-trihydroxy-17&agr;-methylandrostan-3-one to form 17&bgr;-hydroxy-17&agr;-methyl-1-oxo-1,2,-seco-A-nor-5&agr;-androstan-2-oic acid; and (d) reducing the 17&bgr;-hydroxy-17&agr;-methyl-1-oxo-1,2,-seco-A-nor-5&agr;-androstan-2-oic acid to form oxandrolone.

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Wilmington, NC, United States of America

David Wayne Ray, Jr