Reaktion #11816

Reaktionsgleichung

sodium cyanoborohydride

2-(3-amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

ethyl glyoxylate

acetic acid

sodium triacetoxyborohydride

ethyl glyoxylate

acetic acid

→

title compound

Ausbeute 66.3%

(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-acetic acid ethyl ester

Ausbeute 66.3%

Lösungsmittel

1,2-dichloroethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was warmed
2. 2
   Temperaturto reflux for 3 hours
3. 3
   TemperaturThe reaction was then cooled to ambient temperature
4. 4
   workup.STIRRINGthe reaction was stirred at ambient temperature for 18 hours
5. 5
   Extraktionextracted with methylene chloride
6. 6
   TrocknenThe organic layer was dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

To a solution of 2-(3-amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.105 g, 0.26 mmol) in 1,2-dichloroethane (2 mL) was added ethyl glyoxylate (0.050 mL, ˜0.5 mmol, 50% solution in toluene), acetic acid (0.016 mL, 0.28 mmol) and sodium triacetoxyborohydride (0.085 g, 0.40 mmol). The reaction was stirred at ambient temperature for 18 hours. Additional ethyl glyoxylate (0.050 mL, ˜0.5 mmol, 50% solution in toluene) and acetic acid (0.016 mL, 0.28 mmol) were added and the reaction was warmed to reflux for 3 hours. The reaction was then cooled to ambient temperature, sodium cyanoborohydride (˜0.030 g, 0.48 mmol) was added and the reaction was stirred at ambient temperature for 18 hours. The reaction was diluted with water and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel provided the title compound (0.085 g).

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