Imidazole → N-[1-[4-[[t-butyl(dimethyl)silyl]oxy]-3,5-dimethoxyphenyl]ethyl]ethane-1,2-diamine

HRID 420851

반응식

HRID 420851 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12](=O)[CH3:13])[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].[NH:15]1[CH:19]=[CH:18][N:17]=C1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+].C(N)CN.[BH4-].[Na+]>CN(C)C=O.CO.O1CCCC1.C(OCC)(=O)C>[Si:24]([O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH:12]([NH:17][CH2:18][CH2:19][NH2:15])[CH3:13])=[CH:6][C:7]=1[O:10][CH3:11])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26]

참가 물질

11

반응물 6

HCID 795ImidazoleHCID 3301EthylenediamineHCID 17198AcetosyringoneHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 4311764Sodium borohydride

생성물 1

HCID 66658431N-[1-[4-[[t-butyl(dimethyl)silyl]oxy]-3,5-dimethoxyphenyl]ethyl]ethane-1,2-diamine수율 23.1%

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3′,5′-Dimethoxy-4′-hydroxyacetophenone (1.00 g) was dissolved in dimethylformamide (4 ml), the solution was added with imidazole (1.04 g) and t-butyldimethylchlorosilane (769 mg), and the mixture was stirred at room temperature for 10 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was successively washed 3 times with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. This product was dissolved in methanol (20 ml), the solution was added with ethylenediamine (289 mg), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added with a suspension of sodium borohydride (289 mg) in tetrahydrofuran (30 ml), and then added with methanol (6 ml), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1) to obtain the title compound (417 mg).

후처리

  1. customthe layers were separated
  2. washthe organic layer was successively washed 3 times with distilled water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. stirringthe mixture was stirred at room temperature for 15 hours
  8. stirringthe mixture was stirred at room temperature for 1.5 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. additionadded with chloroform and saturated aqueous ammonium chloride
  11. customthe layers were separated
  12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated under reduced pressure
  15. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1)

출처 및 근거

ORD 기록
ord-225b14a7aa4e4fdabc592ca8cc5ed182
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097708B2

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