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

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.

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

ORDレコード

ord-3bbc7e5ac5a74798ab3ef4002e1dcdfe

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07741315B2