17,17-Bis(ethylendioxy)-6-methyleneandrostane → 17,17-(Ethylendioxy)-3-methylenandrostane-5alpha-ol

HRID 1912726Notes

Reaction equation

HRID 1912726 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC(=C)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.[CH2:29]1[CH2:53][O:52][C:31]2([CH2:36][CH2:35][C@H:34]3[C@H:37]4[C@H:47]([CH2:48][CH2:49][C@:32]23[CH3:33])[C@:45]2([CH3:46])[C@:40]([OH:51])([CH2:41][C:42](=O)[CH2:43][CH2:44]2)[CH2:39][CH2:38]4)[O:30]1>>[CH2:29]1[CH2:53][O:52][C:31]2([CH2:36][CH2:35][C@H:34]3[C@H:37]4[C@H:47]([CH2:48][CH2:49][C@:32]23[CH3:33])[C@:45]2([CH3:46])[C@:40]([OH:51])([CH2:41][C:42](=[CH2:1])[CH2:43][CH2:44]2)[CH2:39][CH2:38]4)[O:30]1

Participants

3

Reactant 2

HCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostaneHCID 6913402717,17-(Ethylendioxy)-5alpha-hydroxyandrostane-3-one

Product 1

HCID 6913329517,17-(Ethylendioxy)-3-methylenandrostane-5alpha-olYield 98%

Procedure

Following the procedure described above for the preparation 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (Prepn. 8) and starting from 17,17-(ethylendioxy)-5α-hydroxyandrostane-3-one, 17,17-(ethylendioxy)-3-methylene-androstane-5α-ol was obtained in 98% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.62 (m, 1H), 4.50 (m, 1H), 3.78 (m, 4H), 3.42 (s, 1H), 2.36-1.03 (m, 21H), 0.93 (s, 3H), 0.75 (s, 3H).

Workup

  1. customdescribed above for the preparation 3,3

Sources & evidence

ORD record
ord-73886efe356a42dd98668415038e6e2b
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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