Methanol → (17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

HRID 615563

Reaktionsgleichung

Reaktionsgleichung von HRID 615563
CC(C)(O)[C:3]#[N:4].[C-]#N.[K+].[CH3:10][C@:11]12[CH2:28][CH:27]=[C:26]3[C@@H:16]([CH2:17][CH2:18][C:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][C:21](=[O:29])[CH:20]=4)[C@@H:15]1[CH2:14][CH2:13][C:12]2=[O:30].CO>O>[C:3]([C@@:12]1([OH:30])[CH2:13][CH2:14][C@H:15]2[C@H:16]3[C:26](=[CH:27][CH2:28][C@:11]12[CH3:10])[C@:24]1([CH3:25])[C:19](=[CH:20][C:21](=[O:29])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3)#[N:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6406Acetone CyanohydrinHCID 9032Potassium CyanideHCID 2395959-Dehydroandrostenedione

Produkt 1

HCID 10859900(17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Acetone cyanohydrin (5 ml) and sufficient potassium cyanide to adjust the pH to 9.9 is added to a slurry of androst-4,9(11)-dien-3,17-dione (0,5 g), methanol (40 ml) and water (2.5 g) at 40°. The reaction becomes homogeneous followed by precipitation of the product. After 3.5 hours, water (7.5 ml) is added dropwise and the reaction is allowed slowly to stir at 20°-25° overnight. The slurry is cooled on in ice bath, filtered, the solids washed with methanol/water (1/1) and dried under reduced pressure to give the title compound (4.54 g); [α]D (c=1, CHCl3)=+118°; MS=311, 296 and 284 m/e; NMR (CDCl3)=0.97, 1.37, 2.9, 5.5 and 5.70 δ

Aufarbeitung

  1. customThe reaction becomes homogeneous followed by precipitation of the product
  2. additionwater (7.5 ml) is added dropwise
  3. temperatureThe slurry is cooled on in ice bath
  4. filtrationfiltered
  5. washthe solids washed with methanol/water (1/1)
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8a0849042e164ed8a4ffcaad2463fca1
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04500461

Verknüpfte Notizen

Wird geladen…