p-Toluenesulfonic acid → (8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-one

HRID 1032029

Reaktionsgleichung

Reaktionsgleichung von HRID 1032029
[CH3:1][C@:2]12[CH2:19][CH:18]=[C:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].O1CCOC[CH2:23]1.COC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[CH3:23][O:20][C:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10](=[CH:9][CH2:8][C@@H:7]3[C:17]2=[CH:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C:3]2=[O:21])[CH:11]=1

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 312751,4-DioxaneHCID 2395959-Dehydroandrostenedione

Produkt 1

HCID 13037635(8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

11.5 g of 4,9(11)-androstadiene-3,17-dione [U.S. Pat. No. 3,441,559 (1969)]in 200 ml of dioxane is reacted with 20 ml of orthoformic acid trimethyl ester and 100 mg of p-toluenesulfonic acid. After 48 hours, 5 ml of pyridine is added to the solution, the latter is concentrated under vacuum, the residue taken up in ethyl acetate, washed with water, and dried over sodium sulfate. After chromatography of the crude product with a hexane-ethyl acetate gradient on silica gel containing 2% triethylamine, 9.2 g of 3-methoxy-3,5,9(11)-androstatrien-17-one is isolated; mp 153.4° C.

Aufarbeitung

  1. concentrationthe latter is concentrated under vacuum
  2. washwashed with water
  3. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-8f7441fe1ee14c1497a8aab338e52dc6
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956482

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