17,17-Bis(ethylendioxy)-5alpha-hydroxyandrostan-6-one → HCID 154041431, compound

HRID 42104Notes

Reaction equation

HRID 42104 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]([CH2:16][C:17](=O)[C@:18]5([OH:28])[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.[OH:30]/[N:31]=C1\C[C@@H]2[C@@H]([C@]3(C)C\1CC(=O)CC3)CC[C@@]1(C)[C@H]2CCC1=O>>[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]([CH2:16]/[C:17](=[N:31]\[OH:30])/[C@:18]5([OH:28])[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 8663557917,17-Bis(ethylendioxy)-5alpha-hydroxyandrostan-6-oneHCID 87653583(6E,8R,9S,10R,13S,14S)-6-hydroxyimino-10,13-dimethyl-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

Product 1

HCID 154041431HCID 154041431, compoundYield 85%

Procedure

17,17-Bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyimino-androstane was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxyandrostan-6-one (Prepn. 26) by the procedure described above for the preparation of 6-(E)-hydroxyiminoandrostane-3,17-dione (II-ah, Prepn. 18). The crude was purified by flash chromatography (SiO2, cyclohexane/acetone/CH2Cl2 70/15/15). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.45 (1H, s), 4.33 (1H, s), 3.96-3.69 (8H, m), 2.96 (1H, dd), 2.02-1.08 (18H, m), 0.74 (3H, s), 0.71 (3H, s).

Workup

  1. customThe crude was purified by flash chromatography (SiO2, cyclohexane/acetone/CH2Cl2 70/15/15)

Sources & evidence

ORD record
ord-b450267566264f96bf1fd740441dea73
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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