반응 #1999856

ord-5838251eb4da40749e7fa205593aa84f

반응 방정식

COC[C@@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6β-methoxymethylandrostane
C[C@]12CCC(=O)CC1[C@@H](C#N)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-cyanoandrostane-3,17-dione
→
COC[C@@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
title compound
수율 90.0%
COC[C@@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6β-Methoxymethylandrostane-3,17-dione
수율 90.0%

반응물

COC[C@@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6β-methoxymethylandrostane
C[C@]12CCC(=O)CC1[C@@H](C#N)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-cyanoandrostane-3,17-dione

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척The combined organic extracts were washed with H2O
  2. 2
    건조dried over Na2SO4
  3. 3
    기타evaporated to dryness
  4. 4
    기타The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 70/10/20)

실험 절차

The title compound II-aj was prepared in 90% yield from 3,3:17,17-bis(ethylendioxy)-6β-methoxymethylandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 70/10/20). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.45 (m, 2H), 3.27 (s, 3H), 2.80-0.80 (m, 21H), 1.10 (s, 3H), 0.89 (s, 3H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08609644B2uspto-grants-2013_12