Sodium Hydroxide → N-Formyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

HRID 2073445Notes

Reaction equation

HRID 2073445 reaction equation
[CH3:1][C@@:2]12[C:10](=O)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[C@H:5]1[CH2:4][CH2:3]2.NCCC1C=CC=[CH:27][N:26]=1.[OH-:31].[Na+]>C(O)=O>[CH:27]([NH:26][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:12]([CH2:4][CH2:3][C@:2]12[CH3:1])[C:13]1[CH:14]=[CH:19][C:18]([O:20][CH3:21])=[CH:17][C:16]=1[CH2:15][CH2:5]3)=[O:31]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 759192-PyridineethanamineHCID 92895(+)-Estrone 3-methyl ether

Product 1

HCID 18657691N-Formyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of estrone methyl ether (14.2 g) and 2-(2-aminoethyl)pyridine (24 ml, 24.4 g) is stirred and cooled in an ice bath. To this mixture, formic acid (97-98%, 11.5 ml) is added in portions. The mixture is then heated in an oil bath (180°-190° C. bath temp.) for 24 hours. The mixture is poured onto ice, treated with NaOH, and extracted with methylene chloride (3X). The extracts are dried (Na2SO4), filtered, and concentrated to give a solid. The solid is crystallized from methylene chloride-hexane to give crystals. Recrystallization from methylene chloride-acetone gives the title compound, mp 252°-253° C. preceded by yellowing. (PLA2-, diabetes)

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture is then heated in an oil bath (180°-190° C. bath temp.) for 24 hours
  3. additionThe mixture is poured onto ice
  4. extractionextracted with methylene chloride (3X)
  5. dry with materialThe extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. customThe solid is crystallized from methylene chloride-hexane
  10. customto give crystals
  11. customRecrystallization from methylene chloride-acetone

Sources & evidence

ORD record
ord-b13548cbf9e841a394a59ea2e528d66e
Source dataset
uspto-grants-1990_04
Patent number
US04917826

Reaction notes

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