Reaktion #51826

Reaktionsgleichung

sodium boro hydride

1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

ammonium chloride

→

1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxy-piperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

Ausbeute 26.8%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile being slowly heated to 0° C
2. 2
   Extraktionwas then extracted three times with ethyl acetate
3. 3
   TrocknenThe combined organic layer was dried over anhydrous sodium sulfate
4. 4
   FiltrationThe desiccating agent was filtered off
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=50:1)

Vorschrift

In ethanol (3.0 mL) was dissolved 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (0.13 g), and the solution was cooled to −15° C. Then, sodium boro hydride (26 mg) was added thereto and the resulting mixture was stirred overnight while being slowly heated to 0° C. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, which was then extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=50:1) to obtain 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxy-piperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (35 mg).

Quelle