6b-Oxymorphol synthesis
- Product Name:6b-Oxymorphol
- CAS Number:54934-75-7
- Molecular formula:C17H21NO4
- Molecular Weight:303.35
357-07-3
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Yield:~ 90 % ee
Reaction Conditions:
Stage #1: oxymorphone hydrochloridewith Aminoiminomethanesulfinic acid;sodium hydroxide in water at 65; for 4 h;Inert atmosphere;
Stage #2: with water;ammonium chloride pH=10 - 10.5;
Steps:
1
Example 1Preparation of 6-Beta-Oxymorphol by Reduction of Oxymorphone; The synthesis of 6-beta-oxymorphol is depicted in the following scheme: 1.00 gram of oxymorphone HCl and 1.28 grams of formamidine sulfinic acid (4 equivalents) were added to a three-neck flask that was equipped with a stirrer, a heating apparatus, and a nitrogen source. 10.0 mL of an aqueous solution of 2N NaOH was then added under nitrogen protection. The stirrer is turned on and the mixture was heated to 65° C. The reaction was run for 2 hours at this temperature, wherein the mixture formed a white slurry. After 1 mL of an aqueous solution of 3N NaOH was added to the slurry, a clear solution was produced. The reaction was kept at this temperature for another 2 hours and then cooled. The pH of the reaction solution was adjusted to 10-10.5 using an aqueous solution of saturated NH4Cl. The product precipitated as a white solid and was separated by filtration. The conversion rate was typically greater than 98% at this point. The recovery was typically great than 95%. The stereoselectivity of the beta isomer was about 95:5.
References:
US2009/312552,2009,A1 Location in patent:Page/Page column 7-8
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