Imidazole → N-[2-(benzyloxy)-ethyl]-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-amine

HRID 18011

반응식

HRID 18011 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1.[CH2:20]([O:27][CH2:28][CH:29]=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.ClC(Cl)C>[CH2:20]([O:27][CH2:28][CH2:29][NH:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][Si:11]([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:13])[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

8

반응물 5

HCID 795ImidazoleHCID 258684-Amino-1-butanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 66997788N-[2-(benzyloxy)-ethyl]-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-amine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tert-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine.

후처리

  1. washThe product mixture was washed successively with aqueous NaHCO3, water, and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThis intermediate silylated aminoalcohol was used without further purification
  7. concentrationThe reaction mixture was concentrated under vacuum
  8. customThe residue was partitioned between ethyl acetate and aqueous sodium carbonate
  9. extractionThe organic extract
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customCollection and concentration of appropriate fractions

출처 및 근거

ORD 기록
ord-3bbc7e5ac5a74798ab3ef4002e1dcdfe
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741315B2

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