تفاعل #70388

ord-086cbeb82dba4328b163d8b3b7317183

معادلة التفاعل

C[C@]12CCCCC1=CC(=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-5-androsten-7-one
CC(=O)O[C@H]1CC[C@@]2(C)C(CC(=O)[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrostane-7,17-dione
→
C[C@]12CCCCC1CC(=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-Bis(ethylendioxy)androstane-7-one
المردود 82.0%

المتفاعلات

C[C@]12CCCCC1=CC(=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-5-androsten-7-one
CC(=O)O[C@H]1CC[C@@]2(C)C(CC(=O)[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrostane-7,17-dione

الكواشف

لا شيء

المذيبات

CCOC(C)=O
EtOAc

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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. 29) 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 (8H, m), 2.54-1.10 (20H, m), 1.13 (3H, s), 0.83 (3H, s).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08536160B2uspto-grants-2013_09