6,6-Ethylendioxyandrostane-3beta,17beta-diol → 6,6-Ethylendioxyandrostane-3,17-dione

HRID 1912671Notes

Reaction equation

HRID 1912671 reaction equation
[CH2:1]1[CH2:25][O:24][C:3]2([CH:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C@H:18]([OH:21])[CH2:19]3)[C@@H:14]3[C@H:5]([C@H:6]4[C@@:10]([CH2:12][CH2:13]3)([CH3:11])[C@@H:9]([OH:23])[CH2:8][CH2:7]4)[CH2:4]2)[O:2]1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:25]1[CH2:1][O:2][C:3]2([CH:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH2:19]3)[C@@H:14]3[C@H:5]([C@H:6]4[C@@:10]([CH2:12][CH2:13]3)([CH3:11])[C:9](=[O:23])[CH2:8][CH2:7]4)[CH2:4]2)[O:24]1

Participants

4

Reactant 1

HCID 691334116,6-Ethylendioxyandrostane-3beta,17beta-diol

Product 1

HCID 691334056,6-Ethylendioxyandrostane-3,17-dione

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,6-ethylendioxyandrostane-3β,17β-diol (0.216 g) in CH2Cl2 (8.7 mL) under N2, NMNO (0.217 g), TPAP (10.8 mg) and 4 Å molecular sieves (0.30 g) were added. The mixture was stirred for 1 h and then SiO2 was added. The mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 50/50) to give the title compound II-ag (0.154 g, 72%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.04-3.70 (m, 4H), 2.52-0.82 (m, 20H), 1.18 (s, 3H), 0.88 (s, 3H).

Workup

  1. additionSiO2 was added
  2. customThe mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 50/50)

Sources & evidence

ORD record
ord-380e537d3815476eaacce3a42c3b6a36
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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