Benzhydrylamine → N-Diphenylmethyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

HRID 327928

反応式

HRID 327928 の反応式
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:15][C@@:16]12[C:24](=O)[CH2:23][CH2:22][C@H:21]1[C@@H:20]1[CH2:26][CH2:27][C:28]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=3[C@H:19]1[CH2:18][CH2:17]2.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.C1COCC1>[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][C@H:24]2[CH2:23][CH2:22][C@H:21]3[C@H:20]4[C@H:19]([CH2:18][CH2:17][C@:16]23[CH3:15])[C:29]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:28]=2[CH2:27][CH2:26]4)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 3

HCID 7036BenzhydrylamineHCID 92895(+)-Estrone 3-methyl etherHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 67726218N-Diphenylmethyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒2 回HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of aminodiphenylmethane (5.50 g) in methanol (100 ml) was stirred at room temperature. Added sequentially to this solution were glacial acetic acid (1.8 ml, 1.8 g), estrone methyl ether (8.52 g), sodium cyanoborohydride (2.3 g), and THF (80 ml). The mixture was stirred at room temperature for 8 days. Additional NaB(CN)H3 (1.5 g), amine (5.5 g), and acetic acid (1.8 g) were added after four days of the reaction time. Excess solvent was removed under reduced pressure and water (300 ml) was added to the solid residue. The mixture was made alkaline with 50% aqueous NAOH and was extracted with ether (3×). The extracts were dried (MgSO4), filtered, and concentrated, giving an oily residue. This crude product was chromatographed (500 g silica gel, 5% ethyl acetate-hexane, 350 ml fractions) on a gravity column. The desired product was eluted in fractions 4-7, and after recrystallization from methanol gave a first crop of crystals, mp 127° -129° C., and a second crop. A sample was recrystallized again from methanol and gave an analytical sample of the title compound, mp 127°-129° C. (PLA2, diabetes)

後処理

  1. additionAdded sequentially to this solution
  2. customExcess solvent was removed under reduced pressure and water (300 ml)
  3. additionwas added to the solid residue
  4. extractionwas extracted with ether (3×)
  5. dry with materialThe extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving an oily residue
  9. customThis crude product was chromatographed (500 g silica gel, 5% ethyl acetate-hexane, 350 ml fractions) on a gravity column
  10. washThe desired product was eluted in fractions 4-7
  11. customafter recrystallization from methanol
  12. customgave a first crop of crystals, mp 127° -129° C.
  13. customA sample was recrystallized again from methanol

出典と根拠

ORDレコード
ord-ead6d71e286c44ba81ca13b25c30957d
出典データセット
uspto-grants-1993_12
特許番号
US05274089

関連ノート

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