17,17-Bis(ethylendioxy)androstan-7-one → HCID 178421203, compound

HRID 42111Notes

Reaction equation

HRID 42111 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](=O)[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.C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C/C(=[N:56]\[OH:57])/C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1>>[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](=[N:56]/[OH:57])/[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 6895071317,17-Bis(ethylendioxy)androstan-7-oneHCID 178421204(NE)-N-[(2S,5S,6R,14R,15S)-2,6-dimethyl-18,21,22,25-tetraoxahexacyclo[15.4.4.01,17.02,15.05,14.06,11]pentacosan-12-ylidene]hydroxylamine

Product 1

HCID 178421203HCID 178421203, compoundYield 95%

Procedure

17,17-Bis(ethylendioxy)-7-(E)-hydroxyiminoandrostane was prepared in 95% yield from 3,3:17,17-bis(ethylendioxy)androstan-7-one by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane (Prepn. 18). The crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH 9/1). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.17 (1H, s), 3.88-3.70 (8H, m), 2.89 (1H, m), 2.23-0.71 (19H, m), 0.90 (3H, s), 0.77 (3H, s).

Workup

  1. customThe crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH 9/1)

Sources & evidence

ORD record
ord-c919640376e74a4c9f1be4016bb5e594
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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