Sodium borohydride → 11beta-Fluoro-7alpha-{5-(methyl-nonyl-amino]pentyl}-oestra-1,3,5(10)-triene-3,17beta-diol
Reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:37])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[BH4-].[Na+]>CO>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:37])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
85 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-nonyl-amino]-pentyl}-estra-1,3,5(10)-trien-17-one is dissolved in 3 ml of methanol and mixed with 25 mg of sodium borohydride. After 30 minutes of stirring at room temperature, the solvent is drawn off in a vacuum for the most part, the residue is mixed with common salt solution, extracted 3 times with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative thin-layer chromatography with methylene chloride/methanol=9/1+0.5% triethylamine as a mobile solvent provides 33 mg of 11β-fluoro-7α-{5-[methyl-nonyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol as a foam.
Workup
- additionthe residue is mixed with common salt solution
- extractionextracted 3 times with methylene chloride
- customdried on magnesium sulfate
- concentrationconcentrated by evaporation in a vacuum
Sources & evidence
- ORD record
- ord-34d706f46f3a4fcda7c197d92f447698
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780855B2
Reaction notes
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