Reaktion #46289

Reaktionsgleichung

sodium triacetoxyborohydride

4-hydroxybutylamine

tert-butyldimethyl-silyl chloride

imidazole

benzyloxyacetaldehyde

→

silyloxybutyl-amine

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

Lösungsmittel

dichloromethane

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe product mixture was washed successively with aqueous NaHCO3, water, and brine
2. 2
   ExtraktionThe organic extract
3. 3
   Trocknenwas dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under vacuum
6. 6
   SonstigeThis intermediate silylated aminoalcohol was used without further purification
7. 7
   EinengenThe reaction mixture was concentrated under vacuum
8. 8
   SonstigeThe residue was partitioned between ethyl acetate and aqueous sodium carbonate
9. 9
   ExtraktionThe organic extract
10. 10
    Trocknenwas dried over anhydrous sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated under vacuum
13. 13
    SonstigeCollection and concentration of appropriate fractions

Vorschrift

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.

Quelle