2-(4-Methoxyphenyl)propan-2-amine → N-[1-(4-Methoxyphenyl)-1-methylethyl]-3-oxo-4-androstene-17beta-carboxamide
Reaction equation
[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:21](=[O:29])SC2C=CC=CN=2)=[CH:3]1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH2:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=1>C(Cl)Cl>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH:41][C:21]([C@H:11]2[CH2:10][CH2:9][C@H:8]3[C@H:7]4[C@H:16]([CH2:15][CH2:14][C@:12]23[CH3:13])[C@:17]2([CH3:20])[C:4](=[CH:3][C:2](=[O:1])[CH2:19][CH2:18]2)[CH2:5][CH2:6]4)=[O:29])([CH3:39])[CH3:40])=[CH:34][CH:33]=1Participants
4
Procedure
610 mg of S-2-pyridyl 3-oxo-4-androstene-17β-thiocarboxylate [prepared as described in step (a) above] were dissolved in 1 ml of dry methylene chloride, and 630 mg of 1-(4-methoxyphenyl)-1-methylethylamine (prepared as described in Preparation 10a) were added to the resulting solution. The mixture was then stirred at room temperature for 3 days. At the end of this time, the reaction mixture was subjected, without further treatment, to silica gel column chromatography using a gradient elution method, with mixtures of methylene chloride and acetone in ratios ranging from 3:2 to 1:1 by volume as the eluent, and the product was recrystallized from diisopropyl ether, to give 670 mg of the title compound as white crystals.
Workup
- washa gradient elution method
- customthe product was recrystallized from diisopropyl ether
Sources & evidence
- ORD record
- ord-7fba93c1c5e945c2a688f30b39836621
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717088
Reaction notes
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