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

HRID 18011

Reaktionsgleichung

Reaktionsgleichung von HRID 18011
[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

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3bbc7e5ac5a74798ab3ef4002e1dcdfe
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741315B2

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