Hydrochloric Acid → 3alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

HRID 232793

Reaktionsgleichung

Reaktionsgleichung von HRID 232793
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:1][C@@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[CH2:17][CH2:16][C@@:15]3([CH3:23])[C@H:8]4[CH2:9][CH2:10][C@@H:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 92786Allopregnanolone

Produkt 1

HCID 538852373alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3α-Hydroxy-5α-pregnan-20-one (5.12 g) in pyridine (40 mL) was treated with toluene-p-sulphonyl chloride (5.6 g) , and the reaction mixture was stirred at room temperature for 18.0 h. This solution was poured into dilute (5%) hydrochloric acid (200 mL) and washed three times with chloroform (150 mL portions). The combined organic phase was extracted with more 5% hydrochloric acid and water, dried over magnesium sulfate and evaporated to an oil which on standing crystallized and gave 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one as a white solid.

Aufarbeitung

  1. additionThis solution was poured
  2. washwashed three times with chloroform (150 mL portions)
  3. extractionThe combined organic phase was extracted with more 5% hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to an oil which
  6. customon standing crystallized

Quellen und Nachweise

ORD-Eintrag
ord-ae36d44cf0f74c2187c51d191493e731
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591733

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