17,17-Bis(ethylendioxy)-5-androsten-7-one → 17,17-Bis(ethylendioxy)androstan-7-one

HRID 1912709

Reaktionsgleichung

Reaktionsgleichung von HRID 1912709
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C:16](=[O:28])[CH:17]=[C:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.C(O[C@H]1CC[C@@]2(C)C(CC(=O)[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1)(=O)C>CCOC(C)=O>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C:16](=[O:28])[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:12]1

Komponenten

4

Edukt 2

HCID 6753723417,17-Bis(ethylendioxy)-5-androsten-7-oneHCID 690113133beta-Acetoxyandrostane-7,17-dione

Produkt 1

HCID 6895071317,17-Bis(ethylendioxy)androstan-7-oneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

17,17-Bis(ethylendioxy)androstane-7-one was prepared in 82% yield from 3,3:17,17-bis(ethylendioxy)-5-androsten-7-one by the procedure described above for the preparation of 3β-acetoxyandrostane-7,17-dione (Prepn. 41) using EtOAc instead of EtOH. The crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4). 1H-NMR (300 MHz, acetone-d6, ppm from TMS: δ 3.96-3.75 (m, 8H), 2.54-1.10 (m, 20H), 1.13 (s, 3H), 0.83 (s, 3H).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4)

Quellen und Nachweise

ORD-Eintrag
ord-4fd12f5929a54b6da8ab017e2265ee76
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609644B2

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