Androsta-1,4-diene-3,17-dione → (8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione

HRID 622339

Reaktionsgleichung

Reaktionsgleichung von HRID 622339
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH:9]1[C:10]2[C@:15]([CH3:16])([CH:14]=[CH:13][C:12](=[O:20])[CH:11]=2)[C@@H:17]2[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]2)([CH3:1])[C:3](=[O:21])[CH2:4][CH2:5]3)[CH2:8]1

Komponenten

5

Edukt 2

HCID 13472Androsta-1,4-diene-3,17-dioneHCID 67184N-bromobutanimide

Produkt 1

HCID 25141134(8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dioneAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of 10 g of androsta-1,4-diene-3,17-dione in 95 ml of carbon tetrachloride is refluxed with 6.4 g of N-bromosuccinimide and 0.4 g of benzoyl peroxide for seventy five minutes. After filtration of succinimide, the filtrate was cooled in ice until crystallization is complete. The mixture is then filtered and dried so obtaining 9.8 g of crude 6-bromoandrosta-1,4-diene-3,17-dione satisfactory for the next step. The analytical sample is crystallized from diethyl ether/n-hexane, m.p. 188°-190° C., [α]D20° +116, U.V. (95% EtOH) λmax=250 nm.

Aufarbeitung

  1. filtrationAfter filtration of succinimide
  2. temperaturethe filtrate was cooled in ice until crystallization
  3. filtrationThe mixture is then filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-153aaf94010a4abcb7b32c5ce37ac451
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771043

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