반응 #11732

반응 방정식

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

수율 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

수율 38.4%

용매

ethyl acetate

triethylamine

acetic acid

triethylamine

acetic acid

methanol

반응 조건

후처리

1. 1
   기타To the resulting reaction mixture
2. 2
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature overnight
3. 3
   세척washed with saturated aqueous sodium hydrogen carbonate
4. 4
   건조The organic layer was dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude product was purified by chromatography on silica gel

실험 절차

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).

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