Reaction #70398

ord-d1771f0540504ea385a0197374019030

Reaction equation

C[C@]12CCCCC1C[C@@H](O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7α-hydroxyandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione
→
C[C@]12CCC(=O)CC1C[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
title compound
Yield 89.0%
C[C@]12CCC(=O)CC1C[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
7α-Hydroxyandrostane-3,17-dione
Yield 89.0%

Reactants

C[C@]12CCCCC1C[C@@H](O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7α-hydroxyandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashThe combined organic extracts were washed with H2O
  2. 2
    Dryingdried over Na2SO4
  3. 3
    Otherevaporated to dryness

Procedure

The title compound II-ax was prepared in 89% yield from 3,3:17,17-bis(ethylendioxy)-7α-hydroxyandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300 MHz, dmso-d6, ppm from TMS): δ 4.32 (1H, bb), 3.75 (1H, m), 2.40-1.00 (20H, m), 0.96 (3H, s), 0.78 (3H, s).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09