6alpha-Fluoro-16beta-methyl-17alpha,21-diacetoxypregna-4,9(11)-diene-3,20-dione → 6alpha-Fluoro-16beta-methyl-17alpha,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione
Reaction equation
[F:1][C@@H:2]1[C:25]2[C@:20]([CH3:27])([CH2:21][CH2:22][C:23](=[O:26])[CH:24]=2)[C:19]2[C@H:4]([C@H:5]3[C@:16]([CH3:28])([CH2:17][CH:18]=2)[C@@:8]([O:29][C:30](=[O:32])[CH3:31])([C:9](=[O:15])[CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:33])[CH2:6]3)[CH2:3]1>O1CCOCC1>[F:1][C@@H:2]1[C:25]2[C@:20]([CH3:27])([CH:21]=[CH:22][C:23](=[O:26])[CH:24]=2)[C:19]2[C@H:4]([C@H:5]3[C@:16]([CH3:28])([CH2:17][CH:18]=2)[C@@:8]([O:29][C:30](=[O:32])[CH3:31])([C:9](=[O:15])[CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:33])[CH2:6]3)[CH2:3]1Participants
3
Procedure
A mixture of 5.0 g of 6α-fluoro-16β-methyl-17α,21-diacetoxypregna-4,9(11)-diene-3,20-dione (prepared according to British Pat. No. 1,403,962), 100 ml of dioxane and 3.5 g of 2,3-dichloro-4,6-dicyano-1,4-benzoquinone is refluxed for 10 hours. The mixture is then cooled, filtered and evaporated to dryness. The residue is dissolved in acetone and this solution is then filtered through 100 g of alumina and concentrated to yield 6α-fluoro-16β-methyl-17α,21-diacetoxypregna-1,4,9(11)-triene-3,20-dione which is further purified by recrystallization from acetone:hexane.
Workup
- customprepared
- temperatureThe mixture is then cooled
- filtrationfiltered
- customevaporated to dryness
- dissolutionThe residue is dissolved in acetone
- filtrationthis solution is then filtered through 100 g of alumina
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55fea0fea5f843e6a8f62faafb11dc47
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04278669
Reaction notes
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