HCID 20144008, compound → 17,17-Bis(ethylendioxy)androstan-7-one

HRID 1912750Notes

Reaction equation

HRID 1912750 reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C:16](=C(F)F)[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.C1CCCCC1.C(Cl)Cl.CC(C)=[O:42]>>[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C:16](=[O:42])[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1

Participants

3

Reactant 2

HCID 20144008HCID 20144008, compoundHCID 86651525HCID 86651525, compound

Product 1

HCID 6895071317,17-Bis(ethylendioxy)androstan-7-one

Procedure

Using the same reaction conditions described in Prepn. 31 and starting from 3,3:17,17-bis(ethylendioxy)androstane-7-one (Prepn. 42, 353 mg), 3,3:17,17-bis(ethylendioxy)-7-difluoromethyleneandrostane was obtained after flash chromatography (SiO2; cyclohexane:CH2Cl2:acetone 8:1:1) (115 mg, 30%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.85 (8H, m), 2.10-0.9 (20H, m), 0.96 (3H, s), 0.83 (3H, s).

Workup

  1. customthe same reaction conditions

Sources & evidence

ORD record
ord-ff73df1ebc8c4d61884d47f0a56df658
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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