Sodium Chloride → 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+].[Cl-].[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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
85 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-nonyl-amino]pentyl}oestra-1,3,5(10)-trien-17-one are dissolved in 3 ml of methanol and treated with 25 mg of sodium borohydride. After stirring at room temperature for 30 minutes, the solvent is for the most part stripped off in vacuo, the residue is treated with sodium chloride solution, and the mixture is extracted 3 times with methylene chloride, dried over magnesium sulphate and concentrated in vacuo. Preparative thin-layer chromatography using methylene chloride/methanol=9/1+0.5% triethylamine as a mobile phase leads to 33 mg of 11β-fluoro-7α-{5-[methyl-nonyl-amino]pentyl}-oestra-1,3,5(10)-triene-3,17β-diol as a foam.
Workup
- extractionthe mixture is extracted 3 times with methylene chloride
- dry with materialdried over magnesium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7584fdc7f9b845fb9a870be7f4dff264
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677324B1
Reaction notes
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