Hydrogen Peroxide → 17beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

HRID 27332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 27332
B.[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3.[OH-:28].[Na+].OO>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([C@@H:19]([OH:28])[CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 15341895HCID 15341895, Verbindung

Produkt 1

HCID 1534189617beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled solution (0° C.) of 5 ml. of 1 M borane in tetrahydrofuran in 2.7 ml. of dry tetrahydrofuran was added 500 mg. (1.4 millimole) of the product of Step C. in 2.0 ml. of dry tetrahydrofuran. The clear solution was stirred for 1 hr. at room temperature and then cooled to 0° C. and treated with 5 ml. of 2.5 N sodium hydroxide followed by 4 ml. of 30% hydrogen peroxide. The solution was stirred for 1 hr. at room temperature, diluted with water and extracted with ethyl ether, washed with water, brine, dried and evaporated to an oily crystalline material. The product was washed with cold methanol and pumped dry to give 175 mg. of final product having a m.p. of 167°-170° C.

Aufarbeitung

  1. customTo a cooled solution (0° C.) of 5 ml
  2. additiontreated with 5 ml
  3. stirringThe solution was stirred for 1 hr
  4. extractionextracted with ethyl ether
  5. washwashed with water, brine
  6. customdried
  7. customevaporated to an oily crystalline material
  8. washThe product was washed with cold methanol
  9. custompumped dry
  10. customto give 175 mg

Quellen und Nachweise

ORD-Eintrag
ord-f7b4b13f31f1474b91baa4a400875309
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220775

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