Phenethyl bromide → 1-tert-Butyl 3-methyl (3R,5S)-5-[(2-methylpropyl){[1-(2-phenylethyl)-1H-benzimidazol-2-yl]carbonyl}amino]piperidine-1,3-dicarboxylate

Temperatur

65 °C

To a solution of 1-tert-butyl 3-methyl(3R,5S)-5-[(1H-benzimidazol-2-ylcarbonyl)(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (1.38 g) and (2-bromoethyl)benzene (810 μl) in N,N-dimethylacetamide (30 ml) was added cesium carbonate (2.93 g), and the mixture was stirred at 65° C. for 15 hr. (2-Bromoethyl)benzene (810 μl) was added to the reaction mixture, and the mixture was further stirred at 65° C. for 5 hr. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1) was concentrated under reduced pressure to give the object product (1.40 g).

1. stirringthe mixture was further stirred at 65° C. for 5 hr
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. washa fraction eluted with ethyl acetate-hexane (1:1)
8. concentrationwas concentrated under reduced pressure

ORD-Eintrag

ord-626475dc82794b8cb5bacf75e13e233f

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09045436B2