Hydrochloric Acid → 5alpha-Pregn-2-en-20-one

HRID 2253807

Reaktionsgleichung

Reaktionsgleichung von HRID 2253807
C1(C)C=CC(S(O[C@@H:11]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:17]4[CH2:18][CH2:19][C@@H:20]3[C:21](=[O:23])[CH3:22])[CH2:12]2)(=O)=O)=CC=1.Cl>N1C(C)=CC(C)=CC=1C>[CH3:22][C:21](=[O:23])[C@@H:20]1[C@:24]2([CH3:32])[C@H:17]([C@H:16]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:31])[C@H:13]([CH2:12][CH:11]=[CH:30][CH2:29]2)[CH2:14][CH2:15]3)[CH2:18][CH2:19]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 538852373alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

Produkt 1

HCID 2468835alpha-Pregn-2-en-20-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

The crude product 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one in 30 mL of collidine was refluxed for 1.0 h. The solution was allowed to cool and then poured into cold dilute hydrochloric acid (200 mL) and extracted three times with CH2Cl2 (100 mL portions). The combined organic phase was dried over magnesium sulfate and concentrated. Flash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20) gave 4.65 g (97% yield for the two steps) of 5α-pregn-2-ene-20-one.

Aufarbeitung

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2 (100 mL portions)
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washFlash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20)

Quellen und Nachweise

ORD-Eintrag
ord-650dd25937974c86b884e9a3f00bd814
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05232917

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