Methylamine → 11beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)hexyl]oestra-1,3,5(10)-trien-17-one
Reaction equation
[CH3:1][NH2:2].[F:3][C@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][C:18]2=[O:22])[C@H:14]2[C@H:5]1[C:6]1[CH:7]=[CH:8][C:9]([OH:30])=[CH:10][C:11]=1[CH2:12][C@H:13]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]I>O1CCCC1>[F:3][C@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][C:18]2=[O:22])[C@H:14]2[C@H:5]1[C:6]1[CH:7]=[CH:8][C:9]([OH:30])=[CH:10][C:11]=1[CH2:12][C@H:13]2[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([NH:2][CH3:1])[CH3:28]Participants
4
Procedure
718 mg of methylamine is condensed in a solution of 960 mg of 11β-fluoro-3-hydroxy-7α-(6-iodohexyl)-estra-1,3,5(10)-trien-17-one in 9 ml of anhydrous tetrahydrofuran at −78° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −20° C., it is allowed to come to room temperature to allow excess methylamine to evaporate off. Then, the reaction solution is added to saturated sodium bicarbonate solution, extracted 3 times with ethyl acetate, dried on sodium sulfate and concentrated by evaporation in a vacuum. 763 mg of 11β-fluoro-3-hydroxy-7α-[5-(methyl-amino)-hexyl]-estra-1,3,5(10)-trien-17-one is obtained as a crude product.
Workup
- customwas opened at −20° C.
- customto come to room temperature
- customto evaporate off
- additionThen, the reaction solution is added to saturated sodium bicarbonate solution
- extractionextracted 3 times with ethyl acetate
- customdried on sodium sulfate
- concentrationconcentrated by evaporation in a vacuum
Sources & evidence
- ORD record
- ord-24a00707e21d4ca7b78007e40ec2c4db
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780855B2
Reaction notes
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