Pivaloyl chloride → 7beta-Hydroxy-3beta,15alpha-dipivaloyloxy-5-androsten-17-one
Reaktionsgleichung
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][C@H:6]([OH:23])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]([OH:22])[CH2:10][C:11]2=[O:21])[CH2:3]1.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[OH:23][C@H:6]1[CH:5]=[C:4]2[C@:17]([CH3:20])([CH2:18][CH2:19][C@H:2]([O:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3]2)[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C:11](=[O:21])[CH2:10][C@@H:9]1[O:22][C:11](=[O:21])[C:12]([CH3:14])([CH3:13])[CH3:8]Komponenten
5
Versuchsvorschrift
One gram of 3β,7β,15α-trihydroxy-5-androsten-17-one is dissolved at room temperature in 20 ml of pyridine; 2 ml of pivalic acid chloride as well as 100 mg of 4-dimethylaminopyridine are added to the reaction mixture, and the latter is agitated at room temperature for 48 hours. The reaction mixture is then poured into 250 ml of ice water, stirred for 2 hours at room temperature, the resultant precipitate is vacuum-filtered, washed with water, and dried for 8 hours in a vacuum drying cabinet at 50° C., yielding 1.38 g of 7β-hydroxy-3β,15α-dipivaloyloxy-5-androsten-17-one, mp 195°-197° C.
Aufarbeitung
- stirringstirred for 2 hours at room temperature
- filtrationthe resultant precipitate is vacuum-filtered
- washwashed with water
- customdried for 8 hours in a vacuum
- customdrying cabinet at 50° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-ae2093a34f78490eb090c2d3e77846a0
- Quelldatensatz
- uspto-grants-1984_03
- Patentnummer
- US04435327
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