Reacción #11732

Ecuación de reacción

sodium cyanoborohydride

5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

3-amino-propionic acid methyl ester hydrochloride salt

→

title compound

Rendimiento 38.4%

3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamino)-propionic acid methyl ester

Rendimiento 38.4%

Disolventes

ethyl acetate

triethylamine

acetic acid

triethylamine

acetic acid

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo the resulting reaction mixture
2. 2
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature overnight
3. 3
   Lavadowashed with saturated aqueous sodium hydrogen carbonate
4. 4
   SecadoThe organic layer was dried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by chromatography on silica gel

Procedimiento

To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.075 g, 0.18 mmol) in methanol (2 mL) was added 3-amino-propionic acid methyl ester hydrochloride salt (0.063 g, 0.45 mmol) and the pH of the solution was adjusted to 5–6 with triethylamine and acetic acid. The reaction mixture was stirred at ambient temperature for 1 hour. To the resulting reaction mixture was added sodium cyanoborohydride (0.023 g, 0.36 mmol), and the pH of the solution was again adjusted to pH 5 with acetic acid and triethylamine. The reaction mixture was stirred at ambient temperature overnight, diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give the title compound (0.035 g).

Fuente