HCID 69133284, compound → 7alpha-Formamidoandrostane-3,17-dione

HRID 1912715Notes

Reaction equation

C1CO[C:8]23OCC[O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C@H:16]([NH:28][CH:29]=[O:30])[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22]CC[CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])O1.C([C@@H]1C2[C@](C)(C[CH2:47][C:48](=[O:51])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[CH:29]([NH:28][C@@H:16]1[CH2:17][CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:47][C:48](=[O:51])[CH2:19]2)[C@@H:25]2[C@@H:15]1[C@H:6]1[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:12])[CH2:8][CH2:7]1)=[O:30]

Participants

Reactant 2

HCID 69133284HCID 69133284, compound

HCID 86635590HCID 86635590, compound

Product 1

HCID 866515127alpha-Formamidoandrostane-3,17-dioneYield 97%

Procedure

The title compound II-bu was prepared in 97% yield from 3,3:17,17-bis(ethylendioxy)-7α-formamidoandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The crude product was purified by flash chromatography (SiO2, n-hexane/acetone 70/30). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 8.18 (dd, 1H), 7.97 (d, 1H), 4.13 (m, 1H), 2.90-0.95 (m, 20H), 1.00 (s, 3H), 0.79 (s, 3H).

Workup

customThe crude product was purified by flash chromatography (SiO2, n-hexane/acetone 70/30)

Sources & evidence

ORD record: ord-7383519a303c4b6983f335cf166c0b11
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

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