HCID 67536381, compound → 7alpha-Formylandrostane-3,17-dione

HRID 42122Notes

Reaction equation

[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H]([C@H](C=O)CC5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.C=[C:31]1[CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@H:33]([C@H:34]3[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]3)[CH2:32]1>>[CH:1]([C@@H:32]1[CH2:31][CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@@H:33]1[C@H:34]1[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]1)=[O:2]

Participants

Reactant 2

HCID 67536381HCID 67536381, compound

HCID 86635593HCID 86635593, compound

Product 1

HCID 866355927alpha-Formylandrostane-3,17-dioneYield 85%

Procedure

7α-Formylandrostane-3,17-dione was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7α-formylandrostane (2.36 g) by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 9.95 (1H, d), 2.57-0.80 (21H, m), 0.95 (3H, s), 0.80 (3H, s).

Sources & evidence

ORD record: ord-c8c9487b74514d218f523c0f22b69599
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536160B2

Reaction notes

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