Estradiol → HCID 46238961, compound

HRID 1485877Notes

Reaction equation

HRID 1485877 reaction equation
CO[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C@@H]3[C@@H](CC[C:20]=2[CH:21]=1)[C@H]1[C@@](C)([C@@H](OCOC)CC1)CC3.COCCl.[CH3:31][C@@:32]12[C@@H:40]([OH:41])[CH2:39][CH2:38][C@H:37]1[C@@H:36]1[CH2:42][CH2:43][C:44]3[CH:49]=[C:48]([OH:50])[CH:47]=[CH:46][C:45]=3[C@H:35]1[CH2:34][CH2:33]2.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:3][O:4][CH2:5][CH2:21][CH2:20][CH2:8][CH2:7][CH2:6][C@@H:43]1[CH2:42][C@@H:36]2[C@H:35]([CH2:34][CH2:33][C@@:32]3([CH3:31])[C@H:37]2[CH2:38][CH2:39][CH:40]3[OH:41])[C:45]2[CH:46]=[CH:47][C:48]([OH:50])=[CH:49][C:44]1=2

Participants

5

Reactant 3

HCID 5757EstradiolHCID 81531DiisopropylethylamineHCID 66795793HCID 66795793, compound

Product 1

HCID 46238961HCID 46238961, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene—Chloromethyl methyl ether (7.0 mL, 92.0 mmol) is added to a solution of β-estradiol (5 g, 18.4 mmol) and diisopropylethylamine (16.0 mL 92 mmol) in 100 mL of THF. The reaction mixture is heated to reflux and stirred for 18 hours. The THF is removed in vacuo, and the yellow/brown oil is partitioned between water and CH2Cl2. The organic layer is separated, washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo to give a golden oil. Purification by silica gel column chromatography (10% EtOAc/Hex) affords the title compound as a viscous, clear oil (5.7 g, 86%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. customThe THF is removed in vacuo
  4. customthe yellow/brown oil is partitioned between water and CH2Cl2
  5. customThe organic layer is separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give a golden oil
  11. customPurification by silica gel column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-619a14bbca9d4074a8ee67f155b0de93
Source dataset
uspto-grants-2016_08
Patent number
US09422324B2

Reaction notes

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