Pregna-1,4,17(20)-trien-3-one, 11,21-dihydroxy-, (11β)- → 11beta,21-Dihydroxypregna-4,17-dien-3-one
Reaction equation
[OH:1][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:13]([CH2:14][CH2:15][C:16]2=[CH:17][CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:24])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:23])[CH:6]=[CH:5]1.O[C@H]1C[C@@]2(C)[C@@H](CCC2=CCO)[C@H]2[C@H]1[C@]1(C)C([C@@H](C)C2)=CC(=O)C=C1>>[OH:1][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:13]([CH2:14][CH2:15][C:16]2=[CH:17][CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:24])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]1Participants
Procedure
U.S. Pat. No. 3,770,586 claims an improved process for the production of 11β,21-dihydroxypregna-1,4,17(20)-trien-3-one (Example 1) and 11β,21-dihydroxy-6α-methylpregna-1,4,17(20)-trien-3-one (Example 5) whereby the alkali metal salts of the Δ4 -3-keto 21-hemiester substrates thereof where the acyl radical is that of a dicarboxylic acid of 3 to 12 carbon atoms are 1,2-dehydrogenated by use of S. affinis. Using shake flasks, 11β,21-dihydroxypregna-4,17(20)-dien-3-one 21-hemisuccinate potassium salt at a concentration of 5.0 g/l and medium 1, the desired Δ1,4 -product was produced in 100% yield after 5 days (Example 8). Example 1 uses larger stirred tanks and shows a lower yield. With medium 2, and 2.0-7.0 g/l of 11β,21-dihydroxypregna-4,17(20)-dien-3-one 21-hemisuccinate potassium salt yields of 91.1-96.6% were obtained in 6 days.
Sources & evidence
- ORD record
- ord-c39456b756a64d33929deb7e5c2e1123
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05225335
Reaction notes
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