Acetic Acid → Nandrolone Decanoate

HRID 485632

Reaktionsgleichung

Reaktionsgleichung von HRID 485632
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[C:21](O)(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1.CO.O>[CH3:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:21]([O:11][C@@H:10]1[C@@:2]2([CH3:1])[CH2:3][CH2:4][C@@H:5]3[C@@H:20]4[C:14](=[CH:15][C:16]([CH2:18][CH2:19]4)=[O:17])[CH2:13][CH2:12][C@H:6]3[C@@H:7]2[CH2:8][CH2:9]1)=[O:31]

Komponenten

9

Edukt 4

HCID 176Acetic AcidHCID 2969Decanoic AcidHCID 9904NandroloneHCID 10868Dicyclohexylcarbodiimide

Produkt 1

HCID 9677Nandrolone DecanoateAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred solution of 5,48 g 19-nortestosterone, 4 g decanoic acid, 0.24 g DMAP and 0.19 g pTSA in 35 ml CH2Cl2 is slowly added at 10° C. a solution of 5.6 g DCC in 30 ml CH2Cl2. After 5 h at room temperature 2 ml acetic acid is added. The same work-up procedure as in Example 6 gives 7.6 g of pure 19-nortestosterone decanoate (88% yield) as white crystals from methanol/water. M.P. 35°-36° C.

Quellen und Nachweise

ORD-Eintrag
ord-a747324c27494f3e9207531db3365d42
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537722

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