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

HRID 420851ノート

反応式

HRID 420851 の反応式
[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]

参加物

11

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-225b14a7aa4e4fdabc592ca8cc5ed182
出典データセット
uspto-grants-2012_01
特許番号
US08097708B2

反応ノート

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