Reaction equation
[O:1]1[CH:6]([OH:7])[CH2:5][C@@H:4]([CH:8]([CH3:10])[CH3:9])[CH2:3][CH:2]1[C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[CH:20]([CH2:21][CH:22]([OH:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[C:15](=[O:33])[CH2:14]1)[CH3:12].[OH-].[K+]>CO>[O:1]1[CH:6]([OH:7])[CH2:5][C@@H:4]([CH:8]([CH3:10])[CH3:9])[CH2:3][CH:2]1[C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[CH:20]([CH2:21][CH:22]([OH:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[C:15](=[O:33])[CH2:14]1)[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Epimerization of compound 248 at the C14 position using KOH in MeOH yields 22,29-epoxy-3,29-dihydroxy-14β-stigmastan-15-one (260). Compound 248 is dissolved in MeOH and a solution of KOH in MeOH (25 mg/ml) is added. The mixture is refluxed for 15 minutes then cooled to room temperature. Water is added and the aqueous slurry is extracted with chloroform and then dried over MgSO4. Filtration and concentration gives the crude product that contains an epimeric mixture of compounds 248 and 260. Separation of 248 and 260 is achieved using column chromatography.
Sources & evidence
- ORD record
- ord-e726c310a2c64f7b9a603a40637f771a
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046185
Linked notes
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