HCID 69007680, compound → HCID 69133309, compound

HRID 1912662Notes

Reaction equation

HRID 1912662 reaction equation
[N+]([O-])(O[C@@H]1C2[C@](C)(CCCC2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C24OCCOC2(OCCO4)C3)C1)=O.[N+:32]([O-:56])([O:34][C@@H:35]1[CH:52]2[C@:47]([CH3:54])([CH2:48][CH2:49][C:50](=[O:53])[CH2:51]2)[C@@H:46]2[C@H:37]([C@H:38]3[C@@:42]([CH2:44][CH2:45]2)([CH3:43])[C:41](=[O:55])[CH2:40][CH2:39]3)[CH2:36]1)=[O:33]>>[N+:32]([O-:56])([O:34][C@H:35]1[CH:52]2[C@:47]([CH3:54])([CH2:48][CH2:49][C:50](=[O:53])[CH2:51]2)[C@@H:46]2[C@H:37]([C@H:38]3[C@@:42]([CH2:44][CH2:45]2)([CH3:43])[C:41](=[O:55])[CH2:40][CH2:39]3)[CH2:36]1)=[O:33]

Participants

3

Reactant 2

HCID 69007680HCID 69007680, compoundHCID 86635563HCID 86635563, compound

Product 1

HCID 69133309HCID 69133309, compound

Procedure

Prepared in 75% yield from 3,3:17,17-bis(ethylendioxy)androstane-6α-yl nitrate following the procedure described above for the preparation of 3,17-dioxoandrostane-6α-yl nitrate (II-aa, Prepn 1). The crude product was purified by flash chromatography (SiO2, cyclo-hexane/acetone/CH2Cl2 70/15/15) to give II-ab. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.24 (ddd, 1H), 2.72 (dd, 1H), 2.57-0.96 (m, 19H), 1.25 (s, 3H), 0.90 (s, 3H).

Workup

  1. customPrepared in 75% yield from 3,3
  2. customThe crude product was purified by flash chromatography (SiO2, cyclo-hexane/acetone/CH2Cl2 70/15/15)
  3. customto give II-ab

Sources & evidence

ORD record
ord-1e8c9cf5d90a46f3a69f99a535905f02
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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