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

HRID 375029ノート

反応式

HRID 375029 の反応式
[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

参加物

7

反応物 5

HCID 5870EstroneHCID 133692-ChloroethylamineHCID 24758Sodium hydrideHCID 119047PhenolateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e3861dfe36e7447ebc80c0238d024418
出典データセット
uspto-grants-1996_01
特許番号
US05484584

反応ノート

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