HCID 67536381, compound → HCID 87653511, compound

HRID 42105Notes

Reaction equation

HRID 42105 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]([CH2:16]/[C:17](=[N:29]\[OH:30])/[C@:18]5([OH:28])[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])O1.C=C1C2[C@](C)(CCC(=[O:50])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1>>[OH:28][C@:18]12[CH2:19][C:20](=[O:50])[CH2:21][CH2:22][C@:23]1([CH3:24])[C@@H:25]1[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]1)([CH3:5])[C:3](=[O:12])[CH2:8][CH2:7]3)[CH2:16]/[C:17]/2=[N:29]\[OH:30]

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 154041431HCID 154041431, compound

Product 1

HCID 87653511HCID 87653511, compoundYield 80%

Procedure

The title compound II-aq was prepared in 80% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyiminoandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (I-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20). 1H-NMR (300 MHz, acetone-d6, ppm from TMS: δ 10.72 (1H, s), 5.35 (1H, s), 3.12 (1H, dd), 2.85-1.09 (18H, m), 0.94 (3H, s), 0.78 (3H, s).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20)

Sources & evidence

ORD record
ord-c70e028c83024678a5ac724e041eeac4
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

Loading…