Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylate → HCID 14801334, Verbindung

HRID 1165504

Reaktionsgleichung

Reaktionsgleichung von HRID 1165504
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@:8]12[CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH2:15][C:16]4[C@:21]3([CH3:22])[CH2:20][CH2:19][C:18](=[O:26])[CH:17]=4)[C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[C:27](OC)=[O:28]>C1COCC1>[OH:28][CH2:27][C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:7])[C@:21]1([CH3:22])[C:16](=[CH:17][CH:18]([OH:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3

Komponenten

4

Edukt 2

HCID 165014Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylateHCID 21226445Aluminium lithium hydride3×

Produkt 1

HCID 14801334HCID 14801334, VerbindungAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Approximately 750 ml of dry THF was added to a 3-neck round bottom flask equipped with a condenser, argon bubbler and mechanical stirrer. The flask was cooled to 0° C. and lithium aluminum hydride (LAH) (11.39 g, 0.3 mol) was slowly added. After all of the LAH was added, the flask was warmed to room temperature. A solution of methyl androst-4-ene-3-one-17β-carboxylate (66 g, 0.2 mol) in 600 ml of THF was very slowly added to the LAH slurry. After the addition of the steroid, the reaction mixture was slowly warmed to reflux. After 2 hours the excess LAH was quenched with 11.4 ml water, 11.4 ml 15% sodium hydroxide (NaOH) and 28 ml water. The salts were removed by filtration and washed with approximately 1 liter of warm THF. Concentration of the combined organic solutions afforded 63 g (94%) of 17β-(hydroxymethyl)-androst-4-ene-3-ol as mixture of α and β isomers.

Aufarbeitung

  1. customequipped with a condenser
  2. temperaturethe flask was warmed to room temperature
  3. temperaturethe reaction mixture was slowly warmed to reflux
  4. customAfter 2 hours the excess LAH was quenched with 11.4 ml water, 11.4 ml 15% sodium hydroxide (NaOH) and 28 ml water
  5. customThe salts were removed by filtration
  6. washwashed with approximately 1 liter of warm THF

Quellen und Nachweise

ORD-Eintrag
ord-b2c69886ef72425189c760524cc0a1c8
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910226

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