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

HRID 1741933Notes

Reaction equation

HRID 1741933 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 (3×). 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 (3×)
  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-82772f787f7346849eac40034e107bf1
Source dataset
uspto-grants-1994_08
Patent number
US05334712

Reaction notes

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