3beta-Hydroxyandrostane-7,17-dione → Androstane-3,7,17-trione

HRID 42109

Reaction equation

HRID 42109 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([CH2:5][C:6](=[O:22])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([C:6](=[O:22])[CH2:5][CH:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:21]

Participants

4

Reactant 1

HCID 690080933beta-Hydroxyandrostane-7,17-dione

Product 1

HCID 24833691Androstane-3,7,17-trione

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8ab8d3212ded4e96a8f5bf84504e8c2f
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Linked notes

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