Hydrogen Peroxide → 7alpha-Methyl-4-androstene-3alpha,17beta,19-triol

HRID 371835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371835
C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].[OH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:33]([CH2:34][CH2:35][C@:17]12[CH3:18])[C@:30]1([CH2:31][OH:32])[C:25](=[CH:26][C:27](=[O:36])[CH2:28][CH2:29]1)[CH2:24][C@H:23]3[CH3:37].[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:37][C@@H:23]1[CH2:24][C:25]2[C@:30]([CH2:31][OH:32])([CH2:29][CH2:28][C@@H:27]([OH:36])[CH:26]=2)[C@@H:33]2[C@@H:22]1[C@H:19]1[C@@:17]([CH2:35][CH2:34]2)([CH3:18])[C@@H:16]([OH:15])[CH2:21][CH2:20]1

Komponenten

7

Edukt 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 7058499517beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

Produkt 1

HCID 705832857alpha-Methyl-4-androstene-3alpha,17beta,19-triol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 0.5 M solution of potassium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled to -78° C. in a dry ice-acetone bath. 17β,19-Dihydroxy-7α-methyl-4-androsten-3-one in tetrahydrofuran is added slowly and the reaction mixture is stirred for a period of 2 hours at this temperature, warmed to 0° C., and stirred for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide followed by a 30% hydrogen peroxide solution. Solid potassium carbonate is added and the tetrahydrofuran solution decanted. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered and the filtrate removed by evaporation. The residue is crystallized from acetone to yield 7α-methyl-4-androstene-3α,17β,19-triol.

Aufarbeitung

  1. stirringstirred for an additional two hours
  2. customthe tetrahydrofuran solution decanted
  3. washThe solid residue is washed with fresh tetrahydrofuran
  4. dry with materialthe combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate removed by evaporation
  7. customThe residue is crystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-9ae0561c0cd14b288ff292e288b7e7ee
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04087524

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