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

HRID 327928

반응식

HRID 327928 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-ead6d71e286c44ba81ca13b25c30957d
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274089

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