(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: One gram of 9α-fluoro-11β,21-dihydroxy-16α-methyl-1.4-pregnadiene-3,20-dione is dissolved in 125 ml. of methanol and combined with a solution of 250 mg. of copper(II) acetate in 125 ml. of methanol. The mixture is stirred for 15 minutes at room temperature while passing air therethrough, and then is combined with methylene chloride, washed with 5% ammonium chloride solution and water, and concentrated under vacuum. The thus-obtained product is dissolved in 50 ml. of methanol. The solution is mixed with 165 mg. of potassium cyanide, 1.0 ml. of acetic acid, and 5 g. of manganese(IV) oxide and agitated for 30 minutes at room temperature. Then the mixture is filtered, the filtrate diluted with methylene chloride, washed with water, dried, and concentrated under vacuum. The residue is chromatographed over a silica gel column, recrystallized from acetone/hexane, and the methyl ester of 9α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadiene-21-oic acid is thus produced, m.p. 215° C. washed with 5% ammonium chloride solution and water concentrated under vacuum The thus-obtained product is dissolved in 50 ml The solution is mixed with 165 mg of manganese(IV) oxide and agitated for 30 minutes at room temperature Then the mixture is filtered the filtrate diluted with methylene chloride washed with water dried concentrated under vacuum The residue is chromatographed over a silica gel column recrystallized from acetone/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: One gram of 9α-fluoro-11β,21-dihydroxy-16α-methyl-1.4-pregnadiene-3,20-dione is dissolved in 125 ml. of methanol and combined with a solution of 250 mg. of copper(II) acetate in 125 ml. of methanol. The mixture is stirred for 15 minutes at room temperature while passing air therethrough, and then is combined with methylene chloride, washed with 5% ammonium chloride solution and water, and concentrated under vacuum. The thus-obtained product is dissolved in 50 ml. of methanol. The solution is mixed with 165 mg. of potassium cyanide, 1.0 ml. of acetic acid, and 5 g. of manganese(IV) oxide and agitated for 30 minutes at room temperature. Then the mixture is filtered, the filtrate diluted with methylene chloride, washed with water, dried, and concentrated under vacuum. The residue is chromatographed over a silica gel column, recrystallized from acetone/hexane, and the methyl ester of 9α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadiene-21-oic acid is thus produced, m.p. 215° C. washed with 5% ammonium chloride solution and water concentrated under vacuum The thus-obtained product is dissolved in 50 ml The solution is mixed with 165 mg of manganese(IV) oxide and agitated for 30 minutes at room temperature Then the mixture is filtered the filtrate diluted with methylene chloride washed with water dried concentrated under vacuum The residue is chromatographed over a silica gel column recrystallized from acetone/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: One gram of 9α-fluoro-11β,21-dihydroxy-16α-methyl-1.4-pregnadiene-3,20-dione is dissolved in 125 ml. of methanol and combined with a solution of 250 mg. of copper(II) acetate in 125 ml. of methanol. The mixture is stirred for 15 minutes at room temperature while passing air therethrough, and then is combined with methylene chloride, washed with 5% ammonium chloride solution and water, and concentrated under vacuum. The thus-obtained product is dissolved in 50 ml. of methanol. The solution is mixed with 165 mg. of potassium cyanide, 1.0 ml. of acetic acid, and 5 g. of manganese(IV) oxide and agitated for 30 minutes at room temperature. Then the mixture is filtered, the filtrate diluted with methylene chloride, washed with water, dried, and concentrated under vacuum. The residue is chromatographed over a silica gel column, recrystallized from acetone/hexane, and the methyl ester of 9α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadiene-21-oic acid is thus produced, m.p. 215° C. washed with 5% ammonium chloride solution and water concentrated under vacuum The thus-obtained product is dissolved in 50 ml The solution is mixed with 165 mg of manganese(IV) oxide and agitated for 30 minutes at room temperature Then the mixture is filtered the filtrate diluted with methylene chloride washed with water dried concentrated under vacuum The residue is chromatographed over a silica gel column recrystallized from acetone/hexane