Reaktion #70387

ord-8ab8d3212ded4e96a8f5bf84504e8c2f

Reaktionsgleichung

C[C@]12CC[C@H](O)CC1CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrostane-7,17-dione
→
C[C@]12CCC(=O)CC1CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
title compound
C[C@]12CCC(=O)CC1CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
Androstane-3,7,17-trione

Edukte

—
powder
C[C@]12CC[C@H](O)CC1CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrostane-7,17-dione

Reagenzien

CCC[N+](CCC)(CCC)CCC.[O]=[Ru](=[O])(=[O])[O-]
TPAP

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationAfter 0.5 h the mixture was filtered
  2. 2
    Sonstigethe filtrate was purified by flash chromatography (SiO2, CH2Cl2)

Vorschrift

To a stirred solution of 3β-hydroxyandrostane-7,17-dione (1.60 g), TPAP (0.09 mg), NMNO (1.43 g) under N2 in CH2Cl2 (100 mL), molecular sieve type 4 Å powder (2.6 g) was added. After 0.5 h the mixture was filtered and the filtrate was purified by flash chromatography (SiO2, CH2Cl2) to give the title compound II-as (1.29 g, 81%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 2.82-1.12 (20H, m), 1.39 (3H, s), 0.88 (3H, s).

Quelle

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