17,17-Bis(ethylendioxy)androstan-6-one → HCID 86651505, compound

HRID 1912696Notes

Reaction equation

HRID 1912696 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC(=O)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.[CH2:29]1[CH2:42][O:41][C:36]23[O:37][CH2:38][CH2:39][O:40][C:31]2([C@:32]2([CH2:55][CH2:54][C@H:53]4[C@@H:43]([CH2:44][C:45](=[CH2:56])[CH:46]5[C@:51]4([CH3:52])[CH2:50][CH2:49][CH2:48][CH2:47]5)[C@@H:34]2[CH2:35]3)[CH3:33])[O:30]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH2:39]1[CH2:38][O:37][C:36]23[O:41][CH2:42][CH2:29][O:30][C:31]2([C@:32]2([CH2:55][CH2:54][C@H:53]4[C@@H:43]([CH2:44]/[C:45](=[CH:56]\[CH3:1])/[CH:46]5[C@:51]4([CH3:52])[CH2:50][CH2:49][CH2:48][CH2:47]5)[C@@H:34]2[CH2:35]3)[CH3:33])[O:40]1

Participants

4

Reactant 2

HCID 6753591417,17-Bis(ethylendioxy)androstan-6-oneHCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostane

Product 1

HCID 86651505HCID 86651505, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

17,17-Bis(ethylendioxy)-6(E)-ethylidenandrostane was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)androstane-6-one and (ethyl)triphenylphosphonium bromide by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (Prepn. 8). The mixture was purified by flash chromatography (SiO2, cyclohexane/EtOAc 85/15). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.91 (m, 1H), 3.93-3.78 (m, 8H), 2.69 (m, 1H), 2.10-0.85 (m, 22H), 0.81 (s, 3H), 0.66 (s, 3H).

Workup

  1. customThe mixture was purified by flash chromatography (SiO2, cyclohexane/EtOAc 85/15)

Sources & evidence

ORD record
ord-9cf87c9a06a44d86978d6eafff981e89
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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