Sulfuric Acid → (3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one

HRID 1903002

Reaktionsgleichung

Reaktionsgleichung von HRID 1903002
[OH:1][C@@:2]12[CH2:19][C@@H:18]([O:20]C(=O)C(C)(C)C)[CH2:17][CH2:16][C@:15]1([CH3:27])[C@@H:14]1[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]1)([CH3:11])[C:9](=[O:28])[C@H:8]1[CH2:29][C@@H:7]31)[CH:4]=[CH:3]2.[OH-].[K+].Cl([O-])(=O)(=O)=O.[Na+].S(=O)(=O)(O)O>O1CCCC1.O.CO>[OH:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:27])[C@:2]([OH:1])([CH:3]=[CH:4][C@@H:5]3[C@@H:14]2[CH2:13][CH2:12][C@@:10]2([CH3:11])[C@H:6]3[C@@H:7]3[CH2:29][C@@H:8]3[C:9]2=[O:28])[CH2:19]1

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 522606Sodium PerchlorateHCID 130759725-Hydroxy-15 beta,16 beta-methylene-3 beta-pivaloyloxy-5 beta-androst-6-en-17-one

Produkt 1

HCID 13075974(3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-oneAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

134 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is dissolved in 1340 ml of tetrahydrofuran and 670 ml of methanol and combined in succession with 40 g of pulverized potassium hydroxide and 13 g of sodium perchlorate. After 2.5 hours, the mixture is stirred into 8 l of water, neutralized with 20% sulfuric acid, and the precipitated solid product is removed by filtration. After dissolving in methylene chloride and drying with sodium sulfate, the product is concentrated under vacuum. By trituration of the resultant solid compound with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is obtained, mp 196.5°-198° C.

Aufarbeitung

  1. customthe precipitated solid product is removed by filtration
  2. dissolutionAfter dissolving in methylene chloride
  3. dry with materialdrying with sodium sulfate
  4. concentrationthe product is concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-176988101f7c417e857e3bb56d9f2b4a
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04435327

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