Estrone → 3-(2-Aminoethyl)estra-1,3,5(10)-trien-17-one

HRID 375029Notes

Reaction equation

HRID 375029 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9](O)=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[H-].[Na+].[O-]C1C=CC=CC=1.[H][H].Cl[CH2:33][CH2:34][NH2:35]>CN(C=O)C>[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@@H:14]1[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([CH2:33][CH2:34][NH2:35])[CH:8]=[CH:7][C:6]=3[C@H:5]1[CH2:4][CH2:3]2

Participants

7

Reactant 5

HCID 5870EstroneHCID 133692-ChloroethylamineHCID 24758Sodium hydrideHCID 119047PhenolateHCID 178418361HCID 178418361, compound

Product 1

HCID 441521443-(2-Aminoethyl)estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Estrone (5.0 g, 18.5 mmole) was dissolved in 80 mL of anhydrous DMF. Sodium hydride (4.4 g, 185 mmole) was slowly added to the solution to generate reactive phenoxide in situ. Care was taken to avoid rapid evolution of hydrogen gas. 4.3 g (55 mmole) chloroethylamine was added to the solution and the mixture was allowed to react at 60° C. for 4 hrs. The product was precipitated with a large volume of water and the precipitate collected. For purification, the crude solid was dissolved in methylene chloride, and washed with water. Evaporation of methylene chloride yielded 3-aminoethyl estrone which after washing with ethyl ether gave 3.0 g (52%) of product m.p. 140° C. (decomp.), 3-aminoethyl estrone hydrochloride, m.p. 180° C. (decomp.), 1HNMR (ppm): δ3.01 (2,t,CH2CH2NH2), 2.78 (2,t,CH2,CH2NH2), 4.00 (2,t,COCH2).

Workup

  1. customto react at 60° C. for 4 hrs
  2. customThe product was precipitated with a large volume of water
  3. customthe precipitate collected
  4. customFor purification
  5. dissolutionthe crude solid was dissolved in methylene chloride
  6. washwashed with water
  7. customEvaporation of methylene chloride

Sources & evidence

ORD record
ord-e3861dfe36e7447ebc80c0238d024418
Source dataset
uspto-grants-1996_01
Patent number
US05484584

Reaction notes

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