Ammonia → Oxendolone

HRID 1154783

Reaktionsgleichung

[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:23])[C:17]1[CH:16]=[CH:15][C:14]([O:21]C)=[CH:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2].O1CCCC1.N.[Li]>C(O)(C)(C)C>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:23])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of 2.0 g. of 16β-ethyl-3-methoxy-1,3,5(10)-estratrien-17β-ol in 40 ml. of tetrahydrofuran and 4 ml. of tert.-butanol is added dropwise at -40° C. to 80 ml. of ammonia. After the incremental introduction of 1.2 g. of lithium, the mixture is stirred for 2 hours at -40° C.; then the ammonia is allowed to evaporate, the residue is poured into about 200 ml. of water, and the mixture is extracted with ethyl acetate. The crude product is taken up in 40 ml. of methanol and 4 ml. of 4 N hydrochloric acid and agitated for 15 minutes at 50° C. Thereafter, the mixture is poured into water and extracted with methylene chloride. After recrystallizing the crude product from ethyl acetate/ether, 1.7 g. of 16β-ethyl-17β-hydroxy-4-estren-3-one is produced, m.p. 150°-152° C.

Aufarbeitung

customto evaporate
additionthe residue is poured into about 200 ml
extractionof water, and the mixture is extracted with ethyl acetate
additionThereafter, the mixture is poured into water
extractionextracted with methylene chloride
customAfter recrystallizing the crude product from ethyl acetate/ether, 1.7 g

Quellen und Nachweise

ORD-Eintrag: ord-a7e1eac35c894d3aabd07696fa222da2
Quelldatensatz: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04298538

Verknüpfte Notizen

Wird geladen…