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

HRID 375029노트

반응식

HRID 375029 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3861dfe36e7447ebc80c0238d024418
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484584

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